#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:39:06 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281558 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/90/7159099.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_7159099
loop_
_publ_author_name
'Biswas, Subir'
'Barman, Dipankar'
'Gogoi, Gautam'
'Hoque, Nazimul'
'Devi, Arpita'
'Purkayastha, Siddhartha K.'
'Guha, Ankur Kanti'
'Nath, Jayanta K.'
'Bania, Kusum K.'
_publ_section_title
;
 Heterogeneous iron catalyst for C(1)-H functionalization of 2-naphthols
 with primary aromatic alcohols.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1657
_journal_page_last               1661
_journal_paper_doi               10.1039/d3ob00004d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C18 H16 O3'
_chemical_formula_sum            'C18 H16 O3'
_chemical_formula_weight         280.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2022-11-05 deposited with the CCDC.	2023-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.936(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3525(7)
_cell_length_b                   11.4569(9)
_cell_length_c                   14.7293(11)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.92
_cell_measurement_theta_min      2.44
_cell_volume                     1409.31(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            61407
_diffrn_reflns_theta_full        28.57
_diffrn_reflns_theta_max         28.57
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/2 (Bruker,2014/2)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0446
_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)+(0.0200P)²+0.5967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                2636
_reflns_number_total             3584
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3ob00004d2.cif
_cod_data_source_block           sb1_a
_cod_depositor_comments
'Adding full bibliography for 7159099--7159102.cif.'
_cod_database_code               7159099
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.79708(15) 0.24285(9) 0.48382(8) 0.0546(3) Uani 1 1 d . . .
O3 O 0.70289(17) 1.01836(9) 0.51455(7) 0.0586(3) Uani 1 1 d . . .
H3A H 0.7374 1.0853 0.5123 0.088 Uiso 1 1 calc R . .
O2 O 0.62336(17) 0.55714(10) 0.84146(8) 0.0610(3) Uani 1 1 d . . .
H2 H 0.6502 0.5419 0.8939 0.092 Uiso 1 1 calc R . .
C18 C 0.72787(15) 0.80659(11) 0.70094(8) 0.0321(3) Uani 1 1 d . . .
C9 C 0.65796(16) 0.69969(12) 0.72956(9) 0.0341(3) Uani 1 1 d . . .
C13 C 0.84156(16) 0.86376(12) 0.75903(9) 0.0372(3) Uani 1 1 d . . .
C10 C 0.69824(18) 0.65675(12) 0.81440(9) 0.0412(3) Uani 1 1 d . . .
C5 C 0.61196(16) 0.52968(11) 0.62201(9) 0.0343(3) Uani 1 1 d . . .
C17 C 0.68601(17) 0.86217(11) 0.61764(9) 0.0369(3) Uani 1 1 d . . .
H17 H 0.6136 0.8263 0.5779 0.044 Uiso 1 1 calc R . .
C16 C 0.75080(19) 0.96760(12) 0.59521(9) 0.0417(3) Uani 1 1 d . . .
C8 C 0.53866(17) 0.63179(12) 0.67189(9) 0.0380(3) Uani 1 1 d . . .
H8A H 0.4898 0.6843 0.6278 0.046 Uiso 1 1 calc R . .
H8B H 0.4545 0.6028 0.7105 0.046 Uiso 1 1 calc R . .
C2 C 0.73948(17) 0.34151(12) 0.52691(9) 0.0381(3) Uani 1 1 d . . .
C15 C 0.8639(2) 1.02289(13) 0.65218(11) 0.0488(4) Uani 1 1 d . . .
H15 H 0.9080 1.0942 0.6356 0.059 Uiso 1 1 calc R . .
C7 C 0.76556(19) 0.45348(12) 0.49740(10) 0.0435(3) Uani 1 1 d . . .
H7 H 0.8258 0.4670 0.4459 0.052 Uiso 1 1 calc R . .
C6 C 0.70122(19) 0.54616(12) 0.54514(10) 0.0431(3) Uani 1 1 d . . .
H6 H 0.7188 0.6218 0.5247 0.052 Uiso 1 1 calc R . .
C14 C 0.90814(19) 0.97115(13) 0.73176(11) 0.0465(4) Uani 1 1 d . . .
H14 H 0.9840 1.0074 0.7691 0.056 Uiso 1 1 calc R . .
C4 C 0.5891(2) 0.41566(13) 0.65050(11) 0.0486(4) Uani 1 1 d . . .
H4 H 0.5306 0.4019 0.7026 0.058 Uiso 1 1 calc R . .
C11 C 0.80951(19) 0.71331(14) 0.87153(10) 0.0462(4) Uani 1 1 d . . .
H11 H 0.8345 0.6823 0.9284 0.055 Uiso 1 1 calc R . .
C12 C 0.88075(18) 0.81331(14) 0.84385(10) 0.0450(4) Uani 1 1 d . . .
H12 H 0.9566 0.8491 0.8814 0.054 Uiso 1 1 calc R . .
C3 C 0.6507(2) 0.32245(13) 0.60383(11) 0.0510(4) Uani 1 1 d . . .
H3 H 0.6326 0.2467 0.6240 0.061 Uiso 1 1 calc R . .
C1 C 0.8881(2) 0.25738(16) 0.40376(12) 0.0638(5) Uani 1 1 d . . .
H1B H 0.8244 0.2968 0.3584 0.096 Uiso 1 1 calc R . .
H1A H 0.9196 0.1823 0.3813 0.096 Uiso 1 1 calc R . .
H1C H 0.9819 0.3029 0.4176 0.096 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
C2 O1 C1 118.56(12) . . ?
C16 O3 H3A 109.5 . . ?
C10 O2 H2 109.5 . . ?
C17 C18 C9 123.02(12) . . ?
C17 C18 C13 117.65(12) . . ?
C9 C18 C13 119.30(12) . . ?
C10 C9 C18 118.68(12) . . ?
C10 C9 C8 118.27(12) . . ?
C18 C9 C8 123.04(12) . . ?
C12 C13 C14 121.51(13) . . ?
C12 C13 C18 119.05(13) . . ?
C14 C13 C18 119.40(13) . . ?
O2 C10 C9 117.18(13) . . ?
O2 C10 C11 120.93(13) . . ?
C9 C10 C11 121.89(14) . . ?
C6 C5 C4 117.17(13) . . ?
C6 C5 C8 121.36(12) . . ?
C4 C5 C8 121.46(12) . . ?
C16 C17 C18 120.80(13) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C16 O3 118.13(13) . . ?
C17 C16 C15 121.31(14) . . ?
O3 C16 C15 120.56(13) . . ?
C9 C8 C5 113.65(11) . . ?
C9 C8 H8A 108.8 . . ?
C5 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C5 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C7 C2 C3 119.82(13) . . ?
C7 C2 O1 123.97(13) . . ?
C3 C2 O1 116.20(12) . . ?
C14 C15 C16 119.30(14) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C2 C7 C6 119.35(13) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C5 C6 C7 122.05(13) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C15 C14 C13 121.52(14) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C3 C4 C5 121.75(13) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C12 C11 C10 119.98(14) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 121.04(14) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C4 C3 C2 119.85(13) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1A 109.5 . . ?
H1B C1 H1A 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
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 C2 1.3863(16) . ?
O1 C1 1.4235(19) . ?
O3 C16 1.3764(18) . ?
O3 H3A 0.8200 . ?
O2 C10 1.3640(18) . ?
O2 H2 0.8200 . ?
C18 C17 1.4209(19) . ?
C18 C9 1.4237(19) . ?
C18 C13 1.4270(18) . ?
C9 C10 1.3795(19) . ?
C9 C8 1.5139(19) . ?
C13 C12 1.410(2) . ?
C13 C14 1.411(2) . ?
C10 C11 1.402(2) . ?
C5 C6 1.3787(19) . ?
C5 C4 1.3862(19) . ?
C5 C8 1.5159(18) . ?
C17 C16 1.3663(19) . ?
C17 H17 0.9300 . ?
C16 C15 1.404(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C2 C7 1.3730(19) . ?
C2 C3 1.381(2) . ?
C15 C14 1.359(2) . ?
C15 H15 0.9300 . ?
C7 C6 1.387(2) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C14 H14 0.9300 . ?
C4 C3 1.374(2) . ?
C4 H4 0.9300 . ?
C11 C12 1.357(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C3 H3 0.9300 . ?
C1 H1B 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1C 0.9600 . ?
