#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/44/7124494.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_7124494
loop_
_publ_author_name
'Roy, Subhasish'
'Pradhan, Sourav'
'Punniyamurthy, Tharmalingam'
_publ_section_title
;
 Copper-mediated regioselective C-H etherification of naphthylamides with
 arylboronic acids using water as an oxygen source.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3899
_journal_page_last               3902
_journal_paper_doi               10.1039/c8cc02158a
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C22 H15 F N2 O2'
_chemical_formula_weight         358.36
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-12-28 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                64.897(5)
_cell_angle_beta                 78.682(5)
_cell_angle_gamma                89.685(5)
_cell_formula_units_Z            2
_cell_length_a                   9.1885(7)
_cell_length_b                   9.6792(9)
_cell_length_c                   11.0350(9)
_cell_measurement_temperature    296(2)
_cell_volume                     868.09(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_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  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8038
_diffrn_reflns_theta_full        24.75
_diffrn_reflns_theta_max         24.75
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.096
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0443
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1470
_reflns_number_gt                2157
_reflns_number_total             2872
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc02158a2.cif
_cod_data_source_block           sr-64-1
_cod_database_code               7124494
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C6 C -0.18305(16) 0.08154(16) 0.19847(15) 0.0477(4) Uani 1 1 d .
C1 C -0.19355(17) 0.07640(17) 0.07175(16) 0.0493(4) Uani 1 1 d .
C11 C 0.16769(17) 0.30863(19) 0.12605(15) 0.0529(4) Uani 1 1 d .
C7 C -0.06940(17) 0.16260(19) 0.21899(16) 0.0539(4) Uani 1 1 d .
C21 C 0.04339(18) 0.29463(19) -0.28075(16) 0.0536(4) Uani 1 1 d .
C5 C -0.29698(16) -0.00381(18) 0.31634(17) 0.0549(4) Uani 1 1 d .
C22 C -0.08374(19) 0.18674(18) -0.17809(17) 0.0531(4) Uani 1 1 d .
C14 C 0.40845(18) 0.4385(2) 0.15628(17) 0.0590(5) Uani 1 1 d .
C2 C -0.3083(2) -0.0106(2) 0.06959(19) 0.0682(5) Uani 1 1 d .
H2 H -0.3142 -0.0140 -0.0123 0.082 Uiso 1 1 calc R
C10 C -0.2938(2) -0.0018(2) 0.44295(18) 0.0677(5) Uani 1 1 d .
H10 H -0.3690 -0.0577 0.5189 0.081 Uiso 1 1 calc R
C12 C 0.17457(18) 0.4606(2) 0.09795(16) 0.0590(5) Uani 1 1 d .
H12 H 0.0966 0.5186 0.0688 0.071 Uiso 1 1 calc R
C16 C 0.28243(18) 0.22031(19) 0.16845(16) 0.0591(5) Uani 1 1 d .
H16 H 0.2768 0.1173 0.1865 0.071 Uiso 1 1 calc R
C4 C -0.41191(19) -0.0909(2) 0.3067(2) 0.0676(5) Uani 1 1 d .
H4 H -0.4855 -0.1468 0.3841 0.081 Uiso 1 1 calc R
C13 C 0.29702(19) 0.5269(2) 0.11298(18) 0.0621(5) Uani 1 1 d .
H13 H 0.3037 0.6302 0.0939 0.075 Uiso 1 1 calc R
C15 C 0.40554(19) 0.2871(2) 0.18371(17) 0.0624(5) Uani 1 1 d .
H15 H 0.4846 0.2304 0.2120 0.075 Uiso 1 1 calc R
C8 C -0.0705(2) 0.1617(2) 0.34326(17) 0.0697(5) Uani 1 1 d .
H8 H 0.0056 0.2167 0.3527 0.084 Uiso 1 1 calc R
C9 C -0.1848(2) 0.0790(2) 0.45600(19) 0.0749(6) Uani 1 1 d .
H9 H -0.1853 0.0798 0.5401 0.090 Uiso 1 1 calc R
C3 C -0.4174(2) -0.0949(2) 0.1873(2) 0.0769(6) Uani 1 1 d .
H3 H -0.4940 -0.1540 0.1831 0.092 Uiso 1 1 calc R
C17 C 0.0744(2) 0.3085(2) -0.41236(18) 0.0774(6) Uani 1 1 d .
H17 H 0.0192 0.2485 -0.4374 0.093 Uiso 1 1 calc R
C18 C 0.1876(3) 0.4117(3) -0.5060(2) 0.0945(7) Uani 1 1 d .
H18 H 0.2104 0.4232 -0.5958 0.113 Uiso 1 1 calc R
C19 C 0.2661(2) 0.4969(3) -0.4666(2) 0.0938(7) Uani 1 1 d .
H19 H 0.3446 0.5669 -0.5283 0.113 Uiso 1 1 calc R
C20 C 0.2275(2) 0.4781(3) -0.3333(2) 0.0913(7) Uani 1 1 d .
H20 H 0.2802 0.5390 -0.3074 0.110 Uiso 1 1 calc R
O2 O 0.04473(12) 0.24341(14) 0.10655(11) 0.0672(4) Uani 1 1 d .
O1 O -0.17505(16) 0.13104(16) -0.21495(13) 0.0855(4) Uani 1 1 d .
N1 N -0.08636(14) 0.16266(14) -0.04789(13) 0.0511(4) Uani 1 1 d .
H1 H -0.0121 0.2062 -0.0366 0.061 Uiso 1 1 calc R
N2 N 0.11893(16) 0.37748(18) -0.23968(15) 0.0693(4) Uani 1 1 d .
F1 F 0.52837(12) 0.50483(14) 0.17266(12) 0.0921(4) 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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 C6 C5 115.87(14)
C7 C6 C1 126.58(14)
C5 C6 C1 117.54(15)
C2 C1 N1 121.05(15)
C2 C1 C6 119.49(15)
N1 C1 C6 119.45(14)
C12 C11 C16 121.33(16)
C12 C11 O2 119.15(14)
C16 C11 O2 119.48(15)
C8 C7 O2 120.97(16)
C8 C7 C6 122.10(15)
O2 C7 C6 116.94(13)
N2 C21 C17 122.94(17)
N2 C21 C22 117.25(14)
C17 C21 C22 119.78(17)
C4 C5 C10 119.90(16)
C4 C5 C6 119.92(16)
C10 C5 C6 120.17(16)
O1 C22 N1 125.73(16)
O1 C22 C21 120.32(15)
N1 C22 C21 113.94(15)
F1 C14 C13 118.08(16)
F1 C14 C15 118.73(15)
C13 C14 C15 123.19(17)
C1 C2 C3 121.69(17)
C9 C10 C5 121.42(16)
C11 C12 C13 119.60(15)
C15 C16 C11 119.00(16)
C3 C4 C5 121.05(17)
C14 C13 C12 118.57(17)
C14 C15 C16 118.30(15)
C7 C8 C9 120.61(18)
C10 C9 C8 119.80(17)
C4 C3 C2 120.29(18)
C18 C17 C21 118.9(2)
C19 C18 C17 119.2(2)
C18 C19 C20 118.6(2)
N2 C20 C19 123.5(2)
C7 O2 C11 118.71(11)
C22 N1 C1 129.00(14)
C20 N2 C21 116.81(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C6 C7 1.418(2)
C6 C5 1.426(2)
C6 C1 1.442(2)
C1 C2 1.363(2)
C1 N1 1.4048(19)
C11 C12 1.367(2)
C11 C16 1.380(2)
C11 O2 1.3928(18)
C7 C8 1.365(2)
C7 O2 1.3878(19)
C21 N2 1.330(2)
C21 C17 1.371(2)
C21 C22 1.493(2)
C5 C4 1.402(2)
C5 C10 1.412(2)
C22 O1 1.2186(19)
C22 N1 1.3497(19)
C14 F1 1.3578(18)
C14 C13 1.358(2)
C14 C15 1.364(2)
C2 C3 1.399(2)
C10 C9 1.340(3)
C12 C13 1.370(2)
C16 C15 1.379(2)
C4 C3 1.345(3)
C8 C9 1.393(2)
C17 C18 1.364(3)
C18 C19 1.350(3)
C19 C20 1.374(3)
C20 N2 1.328(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168351126
