#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/58/4035885.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_4035885
loop_
_publ_author_name
'Chang, Meng-Yang'
'Chen, Han-Yu'
'Tsai, Yu-Lin'
_publ_section_title
;
 Temperature-Controlled Desulfonylative Condensation of α-Sulfonyl
 o-Hydroxyacetophenones and 2-Formyl Azaarenes: Synthesis of Azaaryl
 Aurones and Flavones.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              326
_journal_page_last               337
_journal_paper_doi               10.1021/acs.joc.8b02857
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C18 H11 N O2'
_chemical_formula_weight         273.28
_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   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 92.388(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.0319(11)
_cell_length_b                   5.2142(3)
_cell_length_c                   12.3896(7)
_cell_measurement_reflns_used    2849
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3520
_cell_measurement_theta_min      3.0534
_cell_volume                     1292.97(13)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10384
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.399
_diffrn_reflns_theta_min         2.035
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.7269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0416
_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/[σ²(Fo²)+(0.0554P)²+0.2137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1064
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2140
_reflns_number_total             2646
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b02857_si_001.cif
_cod_data_source_block           180147LT
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035885
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.31041(5) 0.36891(18) 0.76668(8) 0.0191(3) Uani 1 1 d . .
O2 O 0.35871(5) 0.2658(2) 1.03964(8) 0.0272(3) Uani 1 1 d . .
N1 N 0.18177(6) -0.2756(2) 0.82996(9) 0.0187(3) Uani 1 1 d . .
C1 C 0.42726(7) 0.9004(3) 0.74370(12) 0.0227(3) Uani 1 1 d . .
H1 H 0.4414 1.0266 0.6943 0.027 Uiso 1 1 calc R U
C2 C 0.37846(7) 0.7271(3) 0.71010(12) 0.0206(3) Uani 1 1 d . .
H3 H 0.3592 0.7290 0.6387 0.025 Uiso 1 1 calc R U
C3 C 0.35932(6) 0.5517(3) 0.78580(11) 0.0171(3) Uani 1 1 d . .
C4 C 0.30381(7) 0.2352(3) 0.86215(11) 0.0180(3) Uani 1 1 d . .
C5 C 0.26246(7) 0.0378(3) 0.87328(11) 0.0191(3) Uani 1 1 d . .
H9 H 0.2608 -0.0300 0.9443 0.023 Uiso 1 1 calc R U
C6 C 0.21934(7) -0.0892(3) 0.79184(11) 0.0174(3) Uani 1 1 d . .
C7 C 0.21969(7) -0.0259(3) 0.68018(11) 0.0201(3) Uani 1 1 d . .
H7 H 0.2476 0.1075 0.6557 0.024 Uiso 1 1 calc R U
C8 C 0.17947(7) -0.1591(3) 0.60903(11) 0.0208(3) Uani 1 1 d . .
H8 H 0.1791 -0.1190 0.5342 0.025 Uiso 1 1 calc R U
C9 C 0.13833(7) -0.3563(3) 0.64619(12) 0.0202(3) Uani 1 1 d . .
C10 C 0.09480(7) -0.5036(3) 0.57788(12) 0.0253(4) Uani 1 1 d . .
H6 H 0.0918 -0.4685 0.5026 0.030 Uiso 1 1 calc R U
C11 C 0.05722(7) -0.6954(3) 0.61912(13) 0.0282(4) Uani 1 1 d . .
H2 H 0.0282 -0.7929 0.5724 0.034 Uiso 1 1 calc R U
C12 C 0.45639(7) 0.8957(3) 0.84810(12) 0.0236(4) Uani 1 1 d . .
H11 H 0.4904 1.0157 0.8679 0.028 Uiso 1 1 calc R U
C13 C 0.43614(7) 0.7182(3) 0.92272(12) 0.0220(3) Uani 1 1 d . .
H10 H 0.4557 0.7145 0.9939 0.026 Uiso 1 1 calc R U
C14 C 0.38623(7) 0.5446(3) 0.89073(11) 0.0187(3) Uani 1 1 d . .
C15 C 0.35165(7) 0.3409(3) 0.94651(11) 0.0193(3) Uani 1 1 d . .
C16 C 0.14143(7) -0.4099(3) 0.75869(12) 0.0195(3) Uani 1 1 d . .
C17 C 0.06110(7) -0.7496(3) 0.73028(14) 0.0272(4) Uani 1 1 d . .
H5 H 0.0350 -0.8845 0.7581 0.033 Uiso 1 1 calc R U
C18 C 0.10216(7) -0.6097(3) 0.79892(12) 0.0228(3) Uani 1 1 d . .
H4 H 0.1042 -0.6475 0.8740 0.027 Uiso 1 1 calc R U
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
C3 O1 C4 107.07(10)
C6 N1 C16 118.31(12)
C2 C1 C12 122.01(14)
C2 C1 H1 119.0
C12 C1 H1 119.0
C3 C2 C1 116.28(13)
C3 C2 H3 121.9
C1 C2 H3 121.9
C2 C3 O1 123.91(12)
C2 C3 C14 123.25(13)
O1 C3 C14 112.82(12)
C5 C4 O1 124.04(12)
C5 C4 C15 126.60(13)
O1 C4 C15 109.32(11)
C4 C5 C6 129.18(13)
C4 C5 H9 115.4
C6 C5 H9 115.4
N1 C6 C7 122.79(13)
N1 C6 C5 114.46(12)
C7 C6 C5 122.69(13)
C8 C7 C6 119.01(14)
C8 C7 H7 120.5
C6 C7 H7 120.5
C7 C8 C9 120.03(13)
C7 C8 H8 120.0
C9 C8 H8 120.0
C8 C9 C10 123.72(14)
C8 C9 C16 117.55(12)
C10 C9 C16 118.73(14)
C11 C10 C9 120.63(14)
C11 C10 H6 119.7
C9 C10 H6 119.7
C10 C11 C17 120.39(14)
C10 C11 H2 119.8
C17 C11 H2 119.8
C13 C12 C1 120.58(13)
C13 C12 H11 119.7
C1 C12 H11 119.7
C12 C13 C14 118.16(13)
C12 C13 H10 120.9
C14 C13 H10 120.9
C3 C14 C13 119.70(13)
C3 C14 C15 106.85(12)
C13 C14 C15 133.44(13)
O2 C15 C14 130.01(13)
O2 C15 C4 126.06(13)
C14 C15 C4 103.93(12)
N1 C16 C18 118.33(13)
N1 C16 C9 122.30(13)
C18 C16 C9 119.36(13)
C18 C17 C11 120.61(15)
C18 C17 H5 119.7
C11 C17 H5 119.7
C17 C18 C16 120.27(14)
C17 C18 H4 119.9
C16 C18 H4 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.3803(16)
O1 C4 1.3841(17)
O2 C15 1.2211(17)
N1 C6 1.3280(18)
N1 C16 1.3651(17)
C1 C2 1.383(2)
C1 C12 1.397(2)
C1 H1 0.9500
C2 C3 1.376(2)
C2 H3 0.9500
C3 C14 1.3869(19)
C4 C5 1.332(2)
C4 C15 1.4937(19)
C5 C6 1.4595(18)
C5 H9 0.9500
C6 C7 1.4227(19)
C7 C8 1.360(2)
C7 H7 0.9500
C8 C9 1.407(2)
C8 H8 0.9500
C9 C10 1.4158(19)
C9 C16 1.420(2)
C10 C11 1.364(2)
C10 H6 0.9500
C11 C17 1.405(2)
C11 H2 0.9500
C12 C13 1.381(2)
C12 H11 0.9500
C13 C14 1.394(2)
C13 H10 0.9500
C14 C15 1.458(2)
C16 C18 1.409(2)
C17 C18 1.369(2)
C17 H5 0.9500
C18 H4 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168329562
