#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/78/4027837.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_4027837
loop_
_publ_author_name
'Nayyef Aljaar'
'Chandi C. Malakar'
'Jürgen Conrad'
'Wolfgang Frey'
'Uwe Beifuss'
_publ_section_title
;
 Reaction of 1-Nitroso-2-naphthols with α-Functionalized Ketones and
 Related Compounds: The Unexpected Formation of Decarbonylated
 2-Substituted Naphtho[1,2-d][1,3]oxazoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              154
_journal_page_last               166
_journal_paper_doi               10.1021/jo3022956
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C18 H13 N O3'
_chemical_formula_sum            'C18 H13 N O3'
_chemical_formula_weight         291.29
_space_group_IT_number           14
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.755(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2811(8)
_cell_length_b                   21.745(2)
_cell_length_c                   7.6197(8)
_cell_measurement_reflns_used    2123
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      1.87
_cell_volume                     1372.0(2)
_computing_cell_refinement       'Bruker APEXII Software Suite, 2008'
_computing_data_collection       'Bruker APEXII Software Suite, 2008'
_computing_data_reduction        'Bruker APEXII Software Suite, 2008'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'Omega + Phi Scans'
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            23146
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0470
_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)+(0.0405P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                2123
_reflns_number_total             3400
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3022956_si_001.cif
_cod_data_source_block           bei01
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4027837
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
O1 O 0.41317(13) 0.65997(5) 0.27095(14) 0.0212(3) Uani 1 1 d .
N1 N 0.46116(14) 0.65325(6) 0.61023(16) 0.0142(3) Uani 1 1 d .
C1 C 0.54316(17) 0.61347(7) 0.5206(2) 0.0126(3) Uani 1 1 d .
O2 O 0.49696(12) 0.65436(5) 0.78834(13) 0.0160(3) Uani 1 1 d .
C2 C 0.49334(18) 0.61671(7) 0.3288(2) 0.0148(4) Uani 1 1 d .
O3 O 0.21314(13) 0.60847(5) 0.88905(15) 0.0220(3) Uani 1 1 d .
C3 C 0.54451(19) 0.56676(7) 0.2155(2) 0.0174(4) Uani 1 1 d .
H3 H 0.5100 0.5661 0.0961 0.021 Uiso 1 1 calc R
C4 C 0.63993(19) 0.52163(7) 0.2776(2) 0.0180(4) Uani 1 1 d .
H4 H 0.6692 0.4893 0.2003 0.022 Uiso 1 1 calc R
C5 C 0.70079(18) 0.51974(7) 0.4576(2) 0.0150(3) Uani 1 1 d .
C6 C 0.79944(18) 0.47120(7) 0.5106(2) 0.0183(4) Uani 1 1 d .
H6 H 0.8248 0.4397 0.4291 0.022 Uiso 1 1 calc R
C7 C 0.86095(19) 0.46806(8) 0.6792(2) 0.0215(4) Uani 1 1 d .
H7 H 0.9261 0.4342 0.7144 0.026 Uiso 1 1 calc R
C8 C 0.82722(19) 0.51471(8) 0.7973(2) 0.0222(4) Uani 1 1 d .
H8 H 0.8724 0.5133 0.9124 0.027 Uiso 1 1 calc R
C9 C 0.72800(18) 0.56335(7) 0.7485(2) 0.0172(4) Uani 1 1 d .
H9 H 0.7059 0.5950 0.8307 0.021 Uiso 1 1 calc R
C10 C 0.66011(18) 0.56635(7) 0.5798(2) 0.0134(3) Uani 1 1 d .
C11 C 0.38594(18) 0.69558(7) 0.8706(2) 0.0148(3) Uani 1 1 d .
H11A H 0.3626 0.7305 0.7908 0.018 Uiso 1 1 calc R
H11B H 0.4359 0.7123 0.9793 0.018 Uiso 1 1 calc R
C12 C 0.22951(18) 0.66335(7) 0.9150(2) 0.0145(3) Uani 1 1 d .
C13 C 0.09762(18) 0.70115(7) 0.9903(2) 0.0138(3) Uani 1 1 d .
C14 C -0.04142(18) 0.67151(7) 1.0484(2) 0.0176(4) Uani 1 1 d .
H14 H -0.0488 0.6280 1.0416 0.021 Uiso 1 1 calc R
C15 C -0.16794(19) 0.70485(8) 1.1154(2) 0.0210(4) Uani 1 1 d .
H15 H -0.2618 0.6843 1.1552 0.025 Uiso 1 1 calc R
C16 C -0.15825(19) 0.76831(8) 1.1249(2) 0.0213(4) Uani 1 1 d .
H16 H -0.2453 0.7912 1.1717 0.026 Uiso 1 1 calc R
C17 C -0.02168(19) 0.79850(8) 1.0663(2) 0.0188(4) Uani 1 1 d .
H17 H -0.0158 0.8421 1.0721 0.023 Uiso 1 1 calc R
C18 C 0.10663(19) 0.76520(7) 0.9991(2) 0.0160(3) Uani 1 1 d .
H18 H 0.2002 0.7859 0.9592 0.019 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
C1 N1 O2 114.84(12)
N1 C1 C10 130.28(14)
N1 C1 C2 109.80(13)
C10 C1 C2 119.75(13)
N1 O2 C11 107.99(11)
O1 C2 C3 121.27(15)
O1 C2 C1 121.33(14)
C3 C2 C1 117.40(14)
C4 C3 C2 120.77(15)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 123.23(15)
C3 C4 H4 118.4
C5 C4 H4 118.4
C6 C5 C10 119.67(15)
C6 C5 C4 119.31(15)
C10 C5 C4 121.02(14)
C7 C6 C5 121.11(16)
C7 C6 H6 119.4
C5 C6 H6 119.4
C6 C7 C8 119.58(16)
C6 C7 H7 120.2
C8 C7 H7 120.2
C7 C8 C9 120.50(16)
C7 C8 H8 119.7
C9 C8 H8 119.7
C8 C9 C10 120.77(16)
C8 C9 H9 119.6
C10 C9 H9 119.6
C9 C10 C5 118.27(14)
C9 C10 C1 124.58(14)
C5 C10 C1 117.11(14)
O2 C11 C12 111.31(12)
O2 C11 H11A 109.4
C12 C11 H11A 109.4
O2 C11 H11B 109.4
C12 C11 H11B 109.4
H11A C11 H11B 108.0
O3 C12 C13 121.58(14)
O3 C12 C11 120.73(14)
C13 C12 C11 117.69(13)
C18 C13 C14 119.27(14)
C18 C13 C12 122.04(14)
C14 C13 C12 118.66(14)
C15 C14 C13 120.57(15)
C15 C14 H14 119.7
C13 C14 H14 119.7
C14 C15 C16 120.01(15)
C14 C15 H15 120.0
C16 C15 H15 120.0
C15 C16 C17 120.14(15)
C15 C16 H16 119.9
C17 C16 H16 119.9
C16 C17 C18 120.20(16)
C16 C17 H17 119.9
C18 C17 H17 119.9
C17 C18 C13 119.80(15)
C17 C18 H18 120.1
C13 C18 H18 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.2296(18)
N1 C1 1.2994(19)
N1 O2 1.3855(15)
C1 C10 1.476(2)
C1 C2 1.515(2)
O2 C11 1.4341(17)
C2 C3 1.454(2)
O3 C12 1.2169(17)
C3 C4 1.342(2)
C3 H3 0.9500
C4 C5 1.456(2)
C4 H4 0.9500
C5 C6 1.391(2)
C5 C10 1.419(2)
C6 C7 1.377(2)
C6 H6 0.9500
C7 C8 1.387(2)
C7 H7 0.9500
C8 C9 1.387(2)
C8 H8 0.9500
C9 C10 1.398(2)
C9 H9 0.9500
C11 C12 1.515(2)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.488(2)
C13 C18 1.396(2)
C13 C14 1.397(2)
C14 C15 1.378(2)
C14 H14 0.9500
C15 C16 1.384(2)
C15 H15 0.9500
C16 C17 1.387(2)
C16 H16 0.9500
C17 C18 1.389(2)
C17 H17 0.9500
C18 H18 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
O2 N1 C1 C10 4.8(2)
O2 N1 C1 C2 -179.99(11)
C1 N1 O2 C11 -174.15(12)
N1 C1 C2 O1 13.8(2)
C10 C1 C2 O1 -170.42(14)
N1 C1 C2 C3 -166.42(13)
C10 C1 C2 C3 9.4(2)
O1 C2 C3 C4 176.05(15)
C1 C2 C3 C4 -3.7(2)
C2 C3 C4 C5 -1.2(2)
C3 C4 C5 C6 -179.85(15)
C3 C4 C5 C10 0.6(2)
C10 C5 C6 C7 -1.1(2)
C4 C5 C6 C7 179.28(14)
C5 C6 C7 C8 -1.5(2)
C6 C7 C8 C9 2.1(2)
C7 C8 C9 C10 0.0(2)
C8 C9 C10 C5 -2.6(2)
C8 C9 C10 C1 174.87(14)
C6 C5 C10 C9 3.1(2)
C4 C5 C10 C9 -177.28(14)
C6 C5 C10 C1 -174.51(13)
C4 C5 C10 C1 5.1(2)
N1 C1 C10 C9 -12.6(3)
C2 C1 C10 C9 172.60(14)
N1 C1 C10 C5 164.89(15)
C2 C1 C10 C5 -9.9(2)
N1 O2 C11 C12 85.22(14)
O2 C11 C12 O3 3.8(2)
O2 C11 C12 C13 -175.98(12)
O3 C12 C13 C18 -171.31(15)
C11 C12 C13 C18 8.4(2)
O3 C12 C13 C14 6.5(2)
C11 C12 C13 C14 -173.73(14)
C18 C13 C14 C15 -0.7(2)
C12 C13 C14 C15 -178.58(14)
C13 C14 C15 C16 0.3(2)
C14 C15 C16 C17 0.3(2)
C15 C16 C17 C18 -0.5(2)
C16 C17 C18 C13 0.1(2)
C14 C13 C18 C17 0.4(2)
C12 C13 C18 C17 178.28(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71545235
