#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:35:05 +0200 (Sat 23 de Aug de 2025) $
#$Revision: 301870 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/21/7242106.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_7242106
loop_
_publ_author_name
'Zilla, Mahesh K.'
'Mahajan, Sheena'
'Khajuria, Rajni'
'Gupta, Vivek K.'
'Kapoor, Kamal K.'
'Ali, Asif'
_publ_section_title
;
 An efficient synthesis of 4-phenoxy-quinazoline, 2-phenoxy-quinoxaline,
 and 2-phenoxy-pyridine derivatives using aryne chemistry
;
_journal_issue                   6
_journal_name_full               'RSC Advances'
_journal_page_first              3477
_journal_page_last               3483
_journal_paper_doi               10.1039/D0RA09994E
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C23 H16 N2 O3'
_chemical_formula_sum            'C23 H16 N2 O3'
_chemical_formula_weight         368.38
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1kqk3y
_audit_creation_method           SHELXL-97
_audit_update_record
;
2020-04-21 deposited with the CCDC.	2021-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.250(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.076(2)
_cell_length_b                   10.1079(8)
_cell_length_c                   16.921(2)
_cell_measurement_reflns_used    1788
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5720
_cell_measurement_theta_min      3.9380
_cell_volume                     3606.0(6)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction,2010)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek,2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1049
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7234
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.53
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            WHITE
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0445
_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)+(0.0433P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1090
_reflns_number_gt                2176
_reflns_number_total             3530
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ra09994e2.cif
_cod_data_source_block           asif-pyno2
_cod_depositor_comments
;
The following automatic conversions were performed:

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

data item '_symmetry_cell_setting' value 'MONOCLINIC' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 
;
_cod_original_cell_volume        3605.9(6)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7242106
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'
'-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
N1 N 0.07292(7) 0.64452(13) 0.06170(9) 0.0454(4) Uani 1 1 d . . .
O3 O 0.04066(7) 0.86042(11) 0.02876(10) 0.0693(5) Uani 1 1 d . . .
C2 C 0.06361(8) 0.52734(15) 0.09449(10) 0.0380(4) Uani 1 1 d . . .
C3 C 0.01392(8) 0.51012(15) 0.12704(10) 0.0403(4) Uani 1 1 d . . .
H3 H 0.0087 0.4289 0.1500 0.048 Uiso 1 1 calc R . .
C5 C -0.01783(9) 0.73149(15) 0.09388(11) 0.0451(5) Uani 1 1 d . . .
H5 H -0.0440 0.8038 0.0931 0.054 Uiso 1 1 calc R . .
C4 C -0.02856(8) 0.61184(15) 0.12624(10) 0.0384(4) Uani 1 1 d . . .
C7 C 0.10875(8) 0.42061(16) 0.09241(10) 0.0408(4) Uani 1 1 d . . .
C23 C -0.15817(9) 0.65933(17) 0.22529(11) 0.0451(5) Uani 1 1 d . . .
N2 N -0.18189(9) 0.76312(18) 0.26840(10) 0.0608(5) Uani 1 1 d . . .
C6 C 0.03322(9) 0.74051(16) 0.06253(12) 0.0461(5) Uani 1 1 d . . .
C19 C -0.08403(8) 0.58897(16) 0.15658(10) 0.0395(4) Uani 1 1 d . . .
O1 O -0.22553(8) 0.73630(15) 0.29636(10) 0.0831(5) Uani 1 1 d . . .
C24 C -0.10740(8) 0.68728(16) 0.19652(10) 0.0431(5) Uani 1 1 d . . .
H24 H -0.0891 0.7710 0.2038 0.052 Uiso 1 1 calc R . .
C20 C -0.11386(9) 0.46633(17) 0.14607(11) 0.0485(5) Uani 1 1 d . . .
H20 H -0.0991 0.3995 0.1187 0.058 Uiso 1 1 calc R . .
O2 O -0.15677(8) 0.87159(14) 0.27580(10) 0.0848(6) Uani 1 1 d . . .
C8 C 0.16097(9) 0.44497(18) 0.06576(12) 0.0544(5) Uani 1 1 d . . .
H8 H 0.1689 0.5306 0.0514 0.065 Uiso 1 1 calc R . .
C13 C 0.07964(11) 0.87191(16) -0.02239(14) 0.0528(5) Uani 1 1 d . . .
C22 C -0.18739(9) 0.53784(18) 0.21563(12) 0.0530(5) Uani 1 1 d . . .
H22 H -0.2215 0.5216 0.2359 0.064 Uiso 1 1 calc R . .
C9 C 0.20152(10) 0.3444(2) 0.06016(14) 0.0686(6) Uani 1 1 d . . .
H9 H 0.2366 0.3627 0.0424 0.082 Uiso 1 1 calc R . .
C12 C 0.09998(10) 0.29257(17) 0.11487(13) 0.0604(6) Uani 1 1 d . . .
H12 H 0.0659 0.2739 0.1347 0.073 Uiso 1 1 calc R . .
C21 C -0.16465(9) 0.44149(18) 0.17512(12) 0.0552(5) Uani 1 1 d . . .
H21 H -0.1837 0.3585 0.1672 0.066 Uiso 1 1 calc R . .
C10 C 0.19051(10) 0.2175(2) 0.08059(13) 0.0641(6) Uani 1 1 d . . .
H10 H 0.2173 0.1493 0.0752 0.077 Uiso 1 1 calc R . .
C11 C 0.14004(11) 0.19203(19) 0.10882(14) 0.0683(6) Uani 1 1 d . . .
H11 H 0.1327 0.1064 0.1240 0.082 Uiso 1 1 calc R . .
C18 C 0.14423(11) 0.85987(17) 0.00777(14) 0.0628(6) Uani 1 1 d . . .
H18 H 0.1633 0.8382 0.0630 0.075 Uiso 1 1 calc R . .
C14 C 0.05127(11) 0.90638(18) -0.10286(15) 0.0660(6) Uani 1 1 d . . .
H14 H 0.0075 0.9158 -0.1225 0.079 Uiso 1 1 calc R . .
C17 C 0.18064(11) 0.88015(19) -0.04455(17) 0.0722(7) Uani 1 1 d . . .
H17 H 0.2245 0.8717 -0.0247 0.087 Uiso 1 1 calc R . .
C16 C 0.15250(14) 0.91282(19) -0.12572(17) 0.0752(7) Uani 1 1 d . . .
H16 H 0.1772 0.9253 -0.1611 0.090 Uiso 1 1 calc R . .
C15 C 0.08811(13) 0.9270(2) -0.15469(15) 0.0757(7) Uani 1 1 d . . .
H15 H 0.0691 0.9507 -0.2096 0.091 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
C6 N1 C2 117.50(14) . . ?
C6 O3 C13 120.31(13) . . ?
N1 C2 C3 120.80(15) . . ?
N1 C2 C7 116.46(14) . . ?
C3 C2 C7 122.73(14) . . ?
C2 C3 C4 121.21(15) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C4 C5 C6 117.78(15) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C5 C4 C3 117.32(15) . . ?
C5 C4 C19 122.20(15) . . ?
C3 C4 C19 120.45(14) . . ?
C12 C7 C8 117.21(16) . . ?
C12 C7 C2 121.91(15) . . ?
C8 C7 C2 120.87(15) . . ?
C22 C23 C24 122.94(16) . . ?
C22 C23 N2 118.44(16) . . ?
C24 C23 N2 118.62(17) . . ?
O2 N2 O1 123.12(17) . . ?
O2 N2 C23 118.57(17) . . ?
O1 N2 C23 118.30(18) . . ?
N1 C6 O3 119.16(15) . . ?
N1 C6 C5 125.36(15) . . ?
O3 C6 C5 115.47(15) . . ?
C24 C19 C20 118.14(15) . . ?
C24 C19 C4 121.58(15) . . ?
C20 C19 C4 120.28(14) . . ?
C23 C24 C19 119.04(16) . . ?
C23 C24 H24 120.5 . . ?
C19 C24 H24 120.5 . . ?
C21 C20 C19 121.53(16) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C9 C8 C7 120.95(18) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C14 C13 C18 120.88(19) . . ?
C14 C13 O3 117.1(2) . . ?
C18 C13 O3 121.8(2) . . ?
C21 C22 C23 117.80(16) . . ?
C21 C22 H22 121.1 . . ?
C23 C22 H22 121.1 . . ?
C10 C9 C8 120.46(19) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C12 C7 121.93(18) . . ?
C11 C12 H12 119.0 . . ?
C7 C12 H12 119.0 . . ?
C22 C21 C20 120.55(17) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C11 C10 C9 119.45(18) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 119.95(19) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C18 C17 119.3(2) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C13 C14 C15 119.4(2) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
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
N1 C6 1.310(2) . ?
N1 C2 1.3493(19) . ?
O3 C6 1.3704(19) . ?
O3 C13 1.395(2) . ?
C2 C3 1.377(2) . ?
C2 C7 1.476(2) . ?
C3 C4 1.389(2) . ?
C3 H3 0.9300 . ?
C5 C4 1.377(2) . ?
C5 C6 1.384(2) . ?
C5 H5 0.9300 . ?
C4 C19 1.480(2) . ?
C7 C12 1.379(2) . ?
C7 C8 1.379(2) . ?
C23 C22 1.374(2) . ?
C23 C24 1.377(2) . ?
C23 N2 1.460(2) . ?
N2 O2 1.218(2) . ?
N2 O1 1.2232(19) . ?
C19 C24 1.385(2) . ?
C19 C20 1.390(2) . ?
C24 H24 0.9300 . ?
C20 C21 1.374(2) . ?
C20 H20 0.9300 . ?
C8 C9 1.377(2) . ?
C8 H8 0.9300 . ?
C13 C14 1.364(3) . ?
C13 C18 1.370(3) . ?
C22 C21 1.369(2) . ?
C22 H22 0.9300 . ?
C9 C10 1.368(3) . ?
C9 H9 0.9300 . ?
C12 C11 1.371(3) . ?
C12 H12 0.9300 . ?
C21 H21 0.9300 . ?
C10 C11 1.361(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C18 C17 1.376(3) . ?
C18 H18 0.9300 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9300 . ?
C17 C16 1.369(3) . ?
C17 H17 0.9300 . ?
C16 C15 1.367(3) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
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
C6 N1 C2 C3 0.3(3) . . . . ?
C6 N1 C2 C7 179.68(16) . . . . ?
N1 C2 C3 C4 0.8(3) . . . . ?
C7 C2 C3 C4 -178.48(16) . . . . ?
C6 C5 C4 C3 1.8(3) . . . . ?
C6 C5 C4 C19 -176.12(16) . . . . ?
C2 C3 C4 C5 -1.9(3) . . . . ?
C2 C3 C4 C19 176.04(16) . . . . ?
N1 C2 C7 C12 -172.18(18) . . . . ?
C3 C2 C7 C12 7.2(3) . . . . ?
N1 C2 C7 C8 6.2(3) . . . . ?
C3 C2 C7 C8 -174.43(17) . . . . ?
C22 C23 N2 O2 -178.76(18) . . . . ?
C24 C23 N2 O2 1.6(3) . . . . ?
C22 C23 N2 O1 2.2(3) . . . . ?
C24 C23 N2 O1 -177.46(17) . . . . ?
C2 N1 C6 O3 -179.11(17) . . . . ?
C2 N1 C6 C5 -0.4(3) . . . . ?
C13 O3 C6 N1 14.9(3) . . . . ?
C13 O3 C6 C5 -163.97(18) . . . . ?
C4 C5 C6 N1 -0.7(3) . . . . ?
C4 C5 C6 O3 178.06(17) . . . . ?
C5 C4 C19 C24 -36.1(3) . . . . ?
C3 C4 C19 C24 146.06(17) . . . . ?
C5 C4 C19 C20 144.46(18) . . . . ?
C3 C4 C19 C20 -33.4(2) . . . . ?
C22 C23 C24 C19 -0.6(3) . . . . ?
N2 C23 C24 C19 179.13(16) . . . . ?
C20 C19 C24 C23 1.1(3) . . . . ?
C4 C19 C24 C23 -178.37(16) . . . . ?
C24 C19 C20 C21 -0.8(3) . . . . ?
C4 C19 C20 C21 178.65(17) . . . . ?
C12 C7 C8 C9 1.5(3) . . . . ?
C2 C7 C8 C9 -176.98(19) . . . . ?
C6 O3 C13 C14 115.9(2) . . . . ?
C6 O3 C13 C18 -69.3(2) . . . . ?
C24 C23 C22 C21 -0.3(3) . . . . ?
N2 C23 C22 C21 -179.99(17) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C8 C7 C12 C11 -2.0(3) . . . . ?
C2 C7 C12 C11 176.49(19) . . . . ?
C23 C22 C21 C20 0.6(3) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C8 C9 C10 C11 -1.9(4) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
C7 C12 C11 C10 0.5(4) . . . . ?
C14 C13 C18 C17 -1.4(3) . . . . ?
O3 C13 C18 C17 -176.05(17) . . . . ?
C18 C13 C14 C15 1.1(3) . . . . ?
O3 C13 C14 C15 176.02(16) . . . . ?
C13 C18 C17 C16 0.4(3) . . . . ?
C18 C17 C16 C15 0.9(3) . . . . ?
C17 C16 C15 C14 -1.1(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168341930
