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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/62/7226273.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_7226273
loop_
_publ_author_name
'J, SELVAKUMAR'
'Grandhi, Gowri Sankar'
'Sahoo, Harekrishna'
'Baidya, Mahiuddin'
_publ_section_title
;
 Copper-Mediated Etherification of Arenes with Alkoxysilanes Directed by
 (2-Aminophenyl)pyrazole Group
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA18861C
_journal_year                    2016
_chemical_formula_moiety         'C17 H14 N4 O4'
_chemical_formula_sum            'C17 H14 N4 O4'
_chemical_formula_weight         338.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-05-14 deposited with the CCDC.
2016-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.098(2)
_cell_length_b                   8.3128(11)
_cell_length_c                   31.328(6)
_cell_measurement_reflns_used    3644
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      2.70
_cell_volume                     3150.6(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0698
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11977
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        20.891
_diffrn_reflns_theta_max         20.891
_diffrn_reflns_theta_min         1.300
_exptl_absorpt_coefficient_mu    0.105
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0042(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         1660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0424
_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)+(0.0625P)²+0.5653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1221
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1141
_reflns_number_total             1670
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ra18861c2.cif
_cod_data_source_block           302
_cod_database_code               7226273
_shelx_shelxl_version_number     2014/7
_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   0.974
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
C1 C 0.7847(3) 0.3248(4) 0.26648(12) 0.0545(10) Uani 1 1 d . .
H1 H 0.7218 0.2616 0.2698 0.065 Uiso 1 1 calc R U
C2 C 0.8019(3) 0.4058(5) 0.22858(13) 0.0637(11) Uani 1 1 d . .
H2 H 0.7500 0.3985 0.2068 0.076 Uiso 1 1 calc R U
C3 C 0.8954(4) 0.4973(4) 0.22289(13) 0.0639(11) Uani 1 1 d . .
H3 H 0.9069 0.5510 0.1972 0.077 Uiso 1 1 calc R U
C4 C 0.9714(3) 0.5091(4) 0.25498(13) 0.0576(10) Uani 1 1 d . .
H4 H 1.0353 0.5694 0.2509 0.069 Uiso 1 1 calc R U
C5 C 0.9538(3) 0.4317(4) 0.29343(11) 0.0423(9) Uani 1 1 d . .
C6 C 0.8601(3) 0.3366(4) 0.29964(11) 0.0417(9) Uani 1 1 d . .
C7 C 0.7462(3) 0.2138(4) 0.35598(11) 0.0471(10) Uani 1 1 d . .
C8 C 0.7455(3) 0.1112(4) 0.39560(11) 0.0430(9) Uani 1 1 d . .
C9 C 0.8369(3) 0.0476(4) 0.41681(12) 0.0483(10) Uani 1 1 d . .
C10 C 0.8230(3) -0.0451(4) 0.45305(12) 0.0565(11) Uani 1 1 d . .
H10 H 0.8838 -0.0866 0.4675 0.068 Uiso 1 1 calc R U
C11 C 0.7171(4) -0.0749(4) 0.46743(12) 0.0570(10) Uani 1 1 d . .
C12 C 0.6249(3) -0.0166(5) 0.44766(13) 0.0626(11) Uani 1 1 d . .
H12 H 0.5543 -0.0384 0.4579 0.075 Uiso 1 1 calc R U
C13 C 0.6413(3) 0.0757(4) 0.41186(12) 0.0546(10) Uani 1 1 d . .
H13 H 0.5797 0.1165 0.3978 0.066 Uiso 1 1 calc R U
C14 C 1.0797(3) 0.6018(4) 0.33689(13) 0.0545(10) Uani 1 1 d . .
H14 H 1.0690 0.6997 0.3231 0.065 Uiso 1 1 calc R U
C15 C 1.1466(3) 0.5739(5) 0.37086(14) 0.0634(12) Uani 1 1 d . .
H15 H 1.1912 0.6477 0.3850 0.076 Uiso 1 1 calc R U
C16 C 1.1342(3) 0.4125(5) 0.37994(12) 0.0565(10) Uani 1 1 d . .
H16 H 1.1705 0.3604 0.4022 0.068 Uiso 1 1 calc R U
C17 C 1.0327(3) 0.0002(5) 0.41624(16) 0.0915(16) Uani 1 1 d . .
H17A H 1.0478 0.0351 0.4449 0.137 Uiso 1 1 calc R U
H17B H 1.0949 0.0244 0.3983 0.137 Uiso 1 1 calc R U
H17C H 1.0197 -0.1137 0.4161 0.137 Uiso 1 1 calc R U
N1 N 1.0316(2) 0.4599(3) 0.32687(9) 0.0439(8) Uani 1 1 d . .
N2 N 1.0648(2) 0.3400(3) 0.35343(9) 0.0496(8) Uani 1 1 d . .
N3 N 0.8450(3) 0.2514(3) 0.33854(10) 0.0451(8) Uani 1 1 d . .
N4 N 0.7026(4) -0.1745(4) 0.50602(12) 0.0789(11) Uani 1 1 d . .
O1 O 0.6585(2) 0.2601(3) 0.34112(9) 0.0699(8) Uani 1 1 d . .
O2 O 0.93821(19) 0.0807(3) 0.40070(8) 0.0661(8) Uani 1 1 d . .
O3 O 0.7846(3) -0.2228(4) 0.52421(11) 0.1064(12) Uani 1 1 d . .
O4 O 0.6086(3) -0.2069(4) 0.51731(11) 0.1164(14) Uani 1 1 d . .
H1N H 0.905(3) 0.225(4) 0.3507(11) 0.059(13) Uiso 1 1 d . .
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
C2 C1 C6 120.7(4)
C2 C1 H1 119.7
C6 C1 H1 119.7
C3 C2 C1 120.4(4)
C3 C2 H2 119.8
C1 C2 H2 119.8
C4 C3 C2 119.9(4)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 C5 120.3(4)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 120.7(3)
C4 C5 N1 117.5(3)
C6 C5 N1 121.7(3)
C1 C6 C5 118.1(3)
C1 C6 N3 121.5(3)
C5 C6 N3 120.4(3)
O1 C7 N3 122.8(3)
O1 C7 C8 119.2(3)
N3 C7 C8 118.0(3)
C13 C8 C9 117.6(3)
C13 C8 C7 115.3(3)
C9 C8 C7 127.1(3)
O2 C9 C10 122.0(3)
O2 C9 C8 117.6(3)
C10 C9 C8 120.4(3)
C11 C10 C9 118.8(4)
C11 C10 H10 120.6
C9 C10 H10 120.6
C12 C11 C10 123.1(4)
C12 C11 N4 118.3(4)
C10 C11 N4 118.6(4)
C11 C12 C13 116.8(4)
C11 C12 H12 121.6
C13 C12 H12 121.6
C12 C13 C8 123.3(4)
C12 C13 H13 118.4
C8 C13 H13 118.4
N1 C14 C15 106.8(3)
N1 C14 H14 126.6
C15 C14 H14 126.6
C14 C15 C16 105.3(3)
C14 C15 H15 127.4
C16 C15 H15 127.4
N2 C16 C15 112.4(3)
N2 C16 H16 123.8
C15 C16 H16 123.8
O2 C17 H17A 109.5
O2 C17 H17B 109.5
H17A C17 H17B 109.5
O2 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C14 N1 N2 111.7(3)
C14 N1 C5 126.7(3)
N2 N1 C5 121.6(3)
C16 N2 N1 103.8(3)
C7 N3 C6 125.2(3)
C7 N3 H1N 121(2)
C6 N3 H1N 114(2)
O3 N4 O4 123.6(4)
O3 N4 C11 118.3(4)
O4 N4 C11 118.2(4)
C9 O2 C17 120.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.381(5)
C1 C6 1.387(4)
C1 H1 0.9300
C2 C3 1.374(5)
C2 H2 0.9300
C3 C4 1.366(5)
C3 H3 0.9300
C4 C5 1.382(5)
C4 H4 0.9300
C5 C6 1.396(4)
C5 N1 1.427(4)
C6 N3 1.422(4)
C7 O1 1.221(4)
C7 N3 1.351(4)
C7 C8 1.506(5)
C8 C13 1.391(4)
C8 C9 1.394(4)
C9 O2 1.354(4)
C9 C10 1.382(5)
C10 C11 1.380(5)
C10 H10 0.9300
C11 C12 1.365(5)
C11 N4 1.475(5)
C12 C13 1.373(5)
C12 H12 0.9300
C13 H13 0.9300
C14 N1 1.352(4)
C14 C15 1.357(5)
C14 H14 0.9300
C15 C16 1.379(5)
C15 H15 0.9300
C16 N2 1.326(4)
C16 H16 0.9300
C17 O2 1.411(4)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
N1 N2 1.359(3)
N3 H1N 0.85(3)
N4 O3 1.213(4)
N4 O4 1.221(4)
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
C6 C1 C2 C3 1.2(5)
C1 C2 C3 C4 -0.5(6)
C2 C3 C4 C5 -1.1(5)
C3 C4 C5 C6 2.0(5)
C3 C4 C5 N1 -174.8(3)
C2 C1 C6 C5 -0.4(5)
C2 C1 C6 N3 -178.6(3)
C4 C5 C6 C1 -1.2(5)
N1 C5 C6 C1 175.4(3)
C4 C5 C6 N3 177.1(3)
N1 C5 C6 N3 -6.3(5)
O1 C7 C8 C13 0.8(4)
N3 C7 C8 C13 -179.6(3)
O1 C7 C8 C9 179.8(3)
N3 C7 C8 C9 -0.5(5)
C13 C8 C9 O2 179.3(3)
C7 C8 C9 O2 0.3(5)
C13 C8 C9 C10 -1.0(5)
C7 C8 C9 C10 -180.0(3)
O2 C9 C10 C11 -179.5(3)
C8 C9 C10 C11 0.8(5)
C9 C10 C11 C12 -0.3(5)
C9 C10 C11 N4 179.7(3)
C10 C11 C12 C13 0.0(5)
N4 C11 C12 C13 180.0(3)
C11 C12 C13 C8 -0.2(5)
C9 C8 C13 C12 0.7(5)
C7 C8 C13 C12 179.8(3)
N1 C14 C15 C16 -0.5(4)
C14 C15 C16 N2 0.6(4)
C15 C14 N1 N2 0.2(4)
C15 C14 N1 C5 179.3(3)
C4 C5 N1 C14 39.9(4)
C6 C5 N1 C14 -136.8(3)
C4 C5 N1 N2 -141.0(3)
C6 C5 N1 N2 42.3(4)
C15 C16 N2 N1 -0.4(4)
C14 N1 N2 C16 0.1(3)
C5 N1 N2 C16 -179.1(3)
O1 C7 N3 C6 -5.2(5)
C8 C7 N3 C6 175.2(3)
C1 C6 N3 C7 -31.2(5)
C5 C6 N3 C7 150.6(3)
C12 C11 N4 O3 -178.1(4)
C10 C11 N4 O3 1.9(5)
C12 C11 N4 O4 3.6(5)
C10 C11 N4 O4 -176.5(4)
C10 C9 O2 C17 10.4(5)
C8 C9 O2 C17 -169.8(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202608
