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#$Date: 2025-02-01 09:07:15 +0200 (Sat, 01 Feb 2025) $
#$Revision: 297561 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/23/7132376.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_7132376
loop_
_publ_author_name
'Chand, Shiv'
'Sharma, Anup Kumar'
'Pandey, Anand Kumar'
'Singh, Krishna Nand'
_publ_section_title
;
 Synthesis of unsymmetrical ketones via dual catalysed cross-coupling of
 α,β-unsaturated carboxylic acids with aryldiazonium salts
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04898E
_journal_year                    2023
_chemical_formula_sum            'C14 H9 N O'
_chemical_formula_weight         207.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-05-12 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.136(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9049(5)
_cell_length_b                   23.030(3)
_cell_length_c                   11.4621(12)
_cell_measurement_temperature    296(2)
_cell_volume                     1030.1(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.932
_diffrn_measured_fraction_theta_max 0.927
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.932
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12115
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.306
_diffrn_reflns_theta_min         3.839
_exptl_absorpt_coefficient_mu    1.157
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             462
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0045(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0787
_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)+(0.0652P)²+2.3690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1751
_refine_ls_wR_factor_ref         0.1914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1270
_reflns_number_total             1756
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04898e2.cif
_cod_data_source_block           data1_a
_cod_depositor_comments
;

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C H N O'
_cod_original_formula_weight         43.03
_cod_original_formula_units_Z            21
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7132376
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_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
O1 O 0.6375(7) 0.23117(11) 0.3147(2) 0.0399(8) Uani 1 1 d . . . . .
N1 N 0.3087(10) 0.49923(15) 0.6640(3) 0.0478(10) Uani 1 1 d . . . . .
C9 C 0.6633(10) 0.30256(16) 0.5886(3) 0.0296(9) Uani 1 1 d . . . . .
H9 H 0.781441 0.274327 0.631833 0.036 Uiso 1 1 calc R U . . .
C8 C 0.5311(9) 0.28952(15) 0.4770(3) 0.0280(9) Uani 1 1 d . . . . .
C2 C 0.5708(9) 0.17709(15) 0.4876(3) 0.0269(9) Uani 1 1 d . . . . .
C11 C 0.4372(10) 0.39924(16) 0.5712(3) 0.0298(9) Uani 1 1 d . . . . .
C10 C 0.6193(10) 0.35734(16) 0.6351(3) 0.0300(9) Uani 1 1 d . . . . .
H10 H 0.711342 0.366148 0.709016 0.036 Uiso 1 1 calc R U . . .
C7 C 0.4237(10) 0.17268(16) 0.5958(3) 0.0292(9) Uani 1 1 d . . . . .
H7 H 0.328816 0.205282 0.629947 0.035 Uiso 1 1 calc R U . . .
C13 C 0.3595(10) 0.33268(16) 0.4124(3) 0.0302(9) Uani 1 1 d . . . . .
H13 H 0.277534 0.324551 0.336899 0.036 Uiso 1 1 calc R U . . .
C1 C 0.5846(9) 0.23198(16) 0.4198(3) 0.0286(9) Uani 1 1 d . . . . .
C6 C 0.4186(10) 0.11941(16) 0.6530(3) 0.0310(9) Uani 1 1 d . . . . .
H6 H 0.319061 0.116590 0.725263 0.037 Uiso 1 1 calc R U . . .
C3 C 0.7040(10) 0.12705(16) 0.4370(3) 0.0312(9) Uani 1 1 d . . . . .
H3 H 0.796967 0.129208 0.363566 0.037 Uiso 1 1 calc R U . . .
C4 C 0.6990(10) 0.07460(17) 0.4947(3) 0.0353(10) Uani 1 1 d . . . . .
H4 H 0.789467 0.041648 0.460480 0.042 Uiso 1 1 calc R U . . .
C12 C 0.3098(10) 0.38707(16) 0.4585(3) 0.0332(10) Uani 1 1 d . . . . .
H12 H 0.192702 0.415382 0.415110 0.040 Uiso 1 1 calc R U . . .
C5 C 0.5592(10) 0.07095(17) 0.6039(3) 0.0354(10) Uani 1 1 d . . . . .
H5 H 0.560474 0.035778 0.643745 0.042 Uiso 1 1 calc R U . . .
C14 C 0.3728(11) 0.45492(17) 0.6223(3) 0.0361(10) Uani 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 0.0181 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'
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
C10 C9 C8 120.2(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C8 C13 119.2(3) . . ?
C9 C8 C1 122.7(3) . . ?
C13 C8 C1 118.0(3) . . ?
C7 C2 C3 118.8(3) . . ?
C7 C2 C1 123.6(3) . . ?
C3 C2 C1 117.6(3) . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 C14 119.9(3) . . ?
C12 C11 C14 119.7(4) . . ?
C9 C10 C11 119.9(4) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C2 C7 C6 119.9(3) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C12 C13 C8 121.0(4) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
O1 C1 C2 120.7(3) . . ?
O1 C1 C8 118.3(3) . . ?
C2 C1 C8 121.1(3) . . ?
C5 C6 C7 120.7(4) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C13 C12 C11 119.2(4) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C6 C5 C4 119.9(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
N1 C14 C11 177.5(5) . . ?
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
O1 C1 1.230(4) . ?
N1 C14 1.158(5) . ?
C9 C10 1.383(5) . ?
C9 C8 1.394(5) . ?
C9 H9 0.9300 . ?
C8 C13 1.396(5) . ?
C8 C1 1.497(5) . ?
C2 C7 1.391(5) . ?
C2 C3 1.399(5) . ?
C2 C1 1.486(5) . ?
C11 C10 1.391(5) . ?
C11 C12 1.395(5) . ?
C11 C14 1.436(5) . ?
C10 H10 0.9300 . ?
C7 C6 1.391(5) . ?
C7 H7 0.9300 . ?
C13 C12 1.377(5) . ?
C13 H13 0.9300 . ?
C6 C5 1.374(5) . ?
C6 H6 0.9300 . ?
C3 C4 1.378(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(5) . ?
C4 H4 0.9300 . ?
C12 H12 0.9300 . ?
C5 H5 0.9300 . ?
