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#$Date: 2025-10-28 14:40:25 +0200 (Tue, 28 Oct 2025) $
#$Revision: 303050 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/40/7064083.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_7064083
loop_
_publ_author_name
'Salamanca-Perdigón, Kevin'
'Lozano, Johan D.'
'Hurtado-Rodríguez, Diana'
'Becerra, Diana'
'Rojas, Hugo'
'Macías, Mario A.'
'Castillo, Juan-Carlos'
_publ_section_title
;
 Cs2CO3-mediated synthesis of 2-alkoxy-3-cyanopyridines: integrated
 crystallographic, photophysical, and DFT analyses
;
_journal_issue                   42
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18369
_journal_page_last               18383
_journal_paper_doi               10.1039/D5NJ03110A
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C20 H12 Cl N3 O'
_chemical_formula_sum            'C20 H12 Cl N3 O'
_chemical_formula_weight         345.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-07-14 deposited with the CCDC.	2025-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.5417(18)
_cell_length_b                   15.119(3)
_cell_length_c                   24.849(4)
_cell_measurement_reflns_used    1793
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      70.9810
_cell_measurement_theta_min      3.4580
_cell_volume                     1706.3(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5874
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.501
_diffrn_reflns_theta_min         4.606
_diffrn_source
'SuperNova (Cu) micro-focus sealed X-ray Source'
_exptl_absorpt_coefficient_mu    2.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0842
_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)+(0.1449P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2085
_refine_ls_wR_factor_ref         0.2457
_reflns_Friedel_coverage         0.518
_reflns_Friedel_fraction_full    0.779
_reflns_Friedel_fraction_max     0.727
_reflns_number_gt                2192
_reflns_number_total             3181
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5nj03110a2.cif
_cod_data_source_block           2022Uniandes082_Cu_DHR66-JCC_auto
_cod_database_code               7064083
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.706
_shelx_estimated_absorpt_t_max   0.760
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C10 C 0.0676(19) 0.6864(4) 0.1170(2) 0.0786(18) Uani 1 1 d . . . . .
C18 C 1.1111(18) 0.6870(4) 0.4169(2) 0.0776(17) Uani 1 1 d . . . . .
H18 H 1.080453 0.629423 0.428808 0.093 Uiso 1 1 calc R U . . .
C17 C 1.302(2) 0.7405(6) 0.4446(3) 0.090(2) Uani 1 1 d . . . . .
H17 H 1.405198 0.718773 0.474143 0.108 Uiso 1 1 calc R U . . .
C11 C 0.0763(17) 0.7489(4) 0.1581(2) 0.0726(16) Uani 1 1 d . . . . .
H11 H -0.003103 0.805068 0.153196 0.087 Uiso 1 1 calc R U . . .
N1 N 0.7030(12) 0.5775(3) 0.36710(16) 0.0661(12) Uani 1 1 d . . . . .
C1 C 0.5192(15) 0.5238(3) 0.34283(19) 0.0634(14) Uani 1 1 d . . . . .
O1 O 0.4557(12) 0.4439(2) 0.36742(14) 0.0762(13) Uani 1 1 d . . . . .
Cl1 Cl -0.0970(6) 0.71676(14) 0.05614(6) 0.1033(8) Uani 1 1 d . . . . .
C19 C 0.595(2) 0.4268(4) 0.4173(2) 0.0835(19) Uani 1 1 d . . . . .
H19A H 0.797808 0.446398 0.415555 0.100 Uiso 1 1 calc R U . . .
H19B H 0.594697 0.363639 0.423993 0.100 Uiso 1 1 calc R U . . .
C7 C 0.3211(15) 0.6420(3) 0.21450(17) 0.0624(13) Uani 1 1 d . . . . .
C6 C 0.1734(19) 0.4760(3) 0.2736(2) 0.0742(17) Uani 1 1 d . . . . .
C5 C 0.7595(13) 0.6565(3) 0.34238(19) 0.0596(12) Uani 1 1 d . . . . .
C4 C 0.6355(15) 0.6779(3) 0.2936(2) 0.0651(13) Uani 1 1 d . . . . .
H4 H 0.677466 0.732241 0.277797 0.078 Uiso 1 1 calc R U . . .
N2 N -0.0002(19) 0.4267(4) 0.2589(2) 0.099(2) Uani 1 1 d . . . . .
C2 C 0.3866(15) 0.5396(3) 0.29361(18) 0.0628(13) Uani 1 1 d . . . . .
N3 N 0.323(3) 0.5028(6) 0.4954(3) 0.140(4) Uani 1 1 d . . . . .
C3 C 0.4474(14) 0.6188(3) 0.26772(19) 0.0615(13) Uani 1 1 d . . . . .
C12 C 0.2057(15) 0.7254(3) 0.20599(19) 0.0663(14) Uani 1 1 d . . . . .
H12 H 0.215955 0.766940 0.233544 0.080 Uiso 1 1 calc R U . . .
C20 C 0.448(2) 0.4715(5) 0.4614(3) 0.096(3) Uani 1 1 d . . . . .
C8 C 0.3110(18) 0.5810(4) 0.17217(19) 0.0768(18) Uani 1 1 d . . . . .
H8 H 0.389482 0.524731 0.176923 0.092 Uiso 1 1 calc R U . . .
C9 C 0.185(2) 0.6037(4) 0.1231(2) 0.084(2) Uani 1 1 d . . . . .
H9 H 0.180457 0.563272 0.094926 0.101 Uiso 1 1 calc R U . . .
C15 C 1.198(2) 0.8583(5) 0.3834(3) 0.097(2) Uani 1 1 d . . . . .
H15 H 1.227925 0.916160 0.371884 0.116 Uiso 1 1 calc R U . . .
C16 C 1.340(2) 0.8277(5) 0.4280(3) 0.091(2) Uani 1 1 d . . . . .
H16 H 1.462972 0.865213 0.447403 0.109 Uiso 1 1 calc R U . . .
C13 C 0.9631(14) 0.7163(4) 0.3718(2) 0.0638(13) Uani 1 1 d . . . . .
C14 C 1.0086(18) 0.8039(4) 0.3552(3) 0.0796(18) Uani 1 1 d . . . . .
H14 H 0.910847 0.825452 0.324989 0.096 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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C9 C10 C11 122.0(6) . . ?
C9 C10 Cl1 120.1(5) . . ?
C11 C10 Cl1 117.9(5) . . ?
C17 C18 C13 121.8(6) . . ?
C18 C17 C16 119.2(7) . . ?
C12 C11 C10 118.1(5) . . ?
C1 N1 C5 117.0(4) . . ?
N1 C1 C2 125.3(5) . . ?
N1 C1 O1 118.0(5) . . ?
C2 C1 O1 116.7(5) . . ?
C1 O1 C19 116.9(5) . . ?
O1 C19 C20 111.9(7) . . ?
C12 C7 C8 118.3(5) . . ?
C12 C7 C3 119.9(4) . . ?
C8 C7 C3 121.8(5) . . ?
N2 C6 C2 178.0(7) . . ?
N1 C5 C4 121.7(5) . . ?
N1 C5 C13 115.3(4) . . ?
C4 C5 C13 123.0(5) . . ?
C5 C4 C3 120.4(5) . . ?
C1 C2 C3 118.1(5) . . ?
C1 C2 C6 118.7(4) . . ?
C3 C2 C6 123.0(5) . . ?
C2 C3 C4 117.5(5) . . ?
C2 C3 C7 122.7(5) . . ?
C4 C3 C7 119.8(4) . . ?
C11 C12 C7 122.0(5) . . ?
N3 C20 C19 176.4(12) . . ?
C9 C8 C7 120.7(5) . . ?
C10 C9 C8 118.9(5) . . ?
C16 C15 C14 120.4(7) . . ?
C15 C16 C17 120.2(7) . . ?
C18 C13 C14 118.1(6) . . ?
C18 C13 C5 120.5(5) . . ?
C14 C13 C5 121.4(5) . . ?
C15 C14 C13 120.3(7) . . ?
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
C10 C9 1.369(9) . ?
C10 C11 1.390(8) . ?
C10 Cl1 1.749(6) . ?
C18 C17 1.372(10) . ?
C18 C13 1.379(9) . ?
C17 C16 1.392(11) . ?
C11 C12 1.375(8) . ?
N1 C1 1.311(8) . ?
N1 C5 1.367(6) . ?
C1 C2 1.384(8) . ?
C1 O1 1.385(6) . ?
O1 C19 1.415(8) . ?
C19 C20 1.449(11) . ?
C7 C12 1.382(7) . ?
C7 C8 1.400(7) . ?
C7 C3 1.484(7) . ?
C6 N2 1.145(9) . ?
C6 C2 1.452(9) . ?
C5 C4 1.375(8) . ?
C5 C13 1.485(8) . ?
C4 C3 1.394(8) . ?
C2 C3 1.388(7) . ?
N3 C20 1.123(11) . ?
C8 C9 1.389(9) . ?
C15 C16 1.366(12) . ?
C15 C14 1.380(10) . ?
C13 C14 1.404(8) . ?
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
C13 C18 C17 C16 2.4(12) . . . . ?
C9 C10 C11 C12 -0.5(12) . . . . ?
Cl1 C10 C11 C12 -179.9(5) . . . . ?
C5 N1 C1 C2 2.3(9) . . . . ?
C5 N1 C1 O1 -179.2(5) . . . . ?
N1 C1 O1 C19 0.4(8) . . . . ?
C2 C1 O1 C19 179.0(6) . . . . ?
C1 O1 C19 C20 79.8(8) . . . . ?
C1 N1 C5 C4 -1.6(8) . . . . ?
C1 N1 C5 C13 178.6(5) . . . . ?
N1 C5 C4 C3 -0.2(8) . . . . ?
C13 C5 C4 C3 179.5(5) . . . . ?
N1 C1 C2 C3 -1.0(9) . . . . ?
O1 C1 C2 C3 -179.5(5) . . . . ?
N1 C1 C2 C6 -176.2(6) . . . . ?
O1 C1 C2 C6 5.3(8) . . . . ?
C1 C2 C3 C4 -0.9(8) . . . . ?
C6 C2 C3 C4 174.0(5) . . . . ?
C1 C2 C3 C7 179.1(5) . . . . ?
C6 C2 C3 C7 -6.0(9) . . . . ?
C5 C4 C3 C2 1.5(8) . . . . ?
C5 C4 C3 C7 -178.5(5) . . . . ?
C12 C7 C3 C2 134.8(6) . . . . ?
C8 C7 C3 C2 -44.3(9) . . . . ?
C12 C7 C3 C4 -45.2(8) . . . . ?
C8 C7 C3 C4 135.7(7) . . . . ?
C10 C11 C12 C7 -1.1(10) . . . . ?
C8 C7 C12 C11 1.7(10) . . . . ?
C3 C7 C12 C11 -177.5(6) . . . . ?
C12 C7 C8 C9 -0.7(11) . . . . ?
C3 C7 C8 C9 178.4(7) . . . . ?
C11 C10 C9 C8 1.4(13) . . . . ?
Cl1 C10 C9 C8 -179.2(7) . . . . ?
C7 C8 C9 C10 -0.7(12) . . . . ?
C14 C15 C16 C17 1.8(13) . . . . ?
C18 C17 C16 C15 -2.6(13) . . . . ?
C17 C18 C13 C14 -1.2(10) . . . . ?
C17 C18 C13 C5 179.5(6) . . . . ?
N1 C5 C13 C18 8.3(8) . . . . ?
C4 C5 C13 C18 -171.4(6) . . . . ?
N1 C5 C13 C14 -170.9(6) . . . . ?
C4 C5 C13 C14 9.3(9) . . . . ?
C16 C15 C14 C13 -0.6(12) . . . . ?
C18 C13 C14 C15 0.3(10) . . . . ?
C5 C13 C14 C15 179.6(6) . . . . ?
