#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/48/4034870.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_4034870
loop_
_publ_author_name
'Zhang, Sheng'
'Yamamoto, Yoshinori'
'Bao, Ming'
_publ_section_title
;
 Palladium-Catalyzed Ligand-Controlled Regioselective Nucleophilic
 Aromatic Substitution of 1-(Chloromethyl)naphthalenes with
 Arylacetonitriles.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13981
_journal_page_last               13990
_journal_paper_doi               10.1021/acs.joc.8b02343
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C18 H13 Cl O'
_chemical_formula_weight         280.73
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.0549(14)
_cell_length_b                   6.3429(6)
_cell_length_c                   27.394(3)
_cell_measurement_reflns_used    1723
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.60
_cell_measurement_theta_min      2.54
_cell_volume                     2789.7(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL''
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13876
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.265
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0806P)²+0.2884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1488
_reflns_number_gt                1603
_reflns_number_total             2460
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02343_si_003.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2789.6(4)
_cod_original_sg_symbol_H-M      'Pbca '
_cod_database_code               4034870
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.32687(6) 0.21142(15) 0.57989(3) 0.0987(4) Uani 1 1 d .
C1 C 0.36638(12) -0.2785(3) 0.27421(8) 0.0451(6) Uani 1 1 d .
C2 C 0.41298(13) -0.2495(4) 0.35823(8) 0.0500(6) Uani 1 1 d .
C3 C 0.40996(13) -0.0899(4) 0.26312(8) 0.0497(6) Uani 1 1 d .
C4 C 0.36832(13) -0.3567(3) 0.32384(8) 0.0484(6) Uani 1 1 d .
C5 C 0.42166(15) -0.3306(4) 0.40954(8) 0.0550(6) Uani 1 1 d .
C6 C 0.39720(13) -0.1909(4) 0.45118(8) 0.0493(6) Uani 1 1 d .
O1 O 0.44977(14) -0.5061(3) 0.41761(7) 0.0878(7) Uani 1 1 d .
C8 C 0.45657(15) -0.0588(4) 0.34612(9) 0.0601(7) Uani 1 1 d .
H8A H 0.4865 0.0128 0.3700 0.072 Uiso 1 1 calc R
C9 C 0.32437(14) -0.3823(4) 0.23650(9) 0.0601(7) Uani 1 1 d .
H9A H 0.2952 -0.5056 0.2431 0.072 Uiso 1 1 calc R
C10 C 0.41604(15) -0.2536(4) 0.49847(9) 0.0646(7) Uani 1 1 d .
H10A H 0.4437 -0.3804 0.5036 0.078 Uiso 1 1 calc R
C11 C 0.31824(16) -0.5460(4) 0.33652(10) 0.0648(7) Uani 1 1 d .
H11A H 0.3255 -0.5782 0.3705 0.097 Uiso 1 1 calc R
H11B H 0.3364 -0.6635 0.3172 0.097 Uiso 1 1 calc R
H11C H 0.2605 -0.5186 0.3301 0.097 Uiso 1 1 calc R
C12 C 0.35444(14) -0.0042(4) 0.44466(9) 0.0558(6) Uani 1 1 d .
H12A H 0.3402 0.0385 0.4133 0.067 Uiso 1 1 calc R
C13 C 0.32579(16) -0.3053(5) 0.19054(11) 0.0692(8) Uani 1 1 d .
H13A H 0.2981 -0.3786 0.1660 0.083 Uiso 1 1 calc R
C14 C 0.45413(15) 0.0164(4) 0.30008(10) 0.0604(7) Uani 1 1 d .
H14A H 0.4821 0.1407 0.2926 0.073 Uiso 1 1 calc R
C15 C 0.33241(15) 0.1204(4) 0.48400(9) 0.0624(7) Uani 1 1 d .
H15A H 0.3039 0.2464 0.4793 0.075 Uiso 1 1 calc R
C16 C 0.40877(15) -0.0117(4) 0.21423(9) 0.0596(7) Uani 1 1 d .
H16A H 0.4362 0.1131 0.2065 0.072 Uiso 1 1 calc R
C17 C 0.35330(16) 0.0550(4) 0.53004(9) 0.0614(7) Uani 1 1 d .
C18 C 0.36707(17) -0.1213(5) 0.17883(9) 0.0671(7) Uani 1 1 d .
H18A H 0.3665 -0.0718 0.1469 0.081 Uiso 1 1 calc R
C19 C 0.39443(17) -0.1314(5) 0.53781(9) 0.0698(8) Uani 1 1 d .
H19A H 0.4075 -0.1744 0.5693 0.084 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C9 C1 C3 118.5(2)
C9 C1 C4 122.9(2)
C3 C1 C4 118.7(2)
C4 C2 C8 121.1(2)
C4 C2 C5 121.6(2)
C8 C2 C5 117.3(2)
C14 C3 C1 119.9(2)
C14 C3 C16 121.0(2)
C1 C3 C16 119.1(2)
C2 C4 C1 119.2(2)
C2 C4 C11 121.7(2)
C1 C4 C11 119.0(2)
O1 C5 C6 119.9(2)
O1 C5 C2 121.0(2)
C6 C5 C2 119.0(2)
C12 C6 C10 118.3(2)
C12 C6 C5 122.7(2)
C10 C6 C5 119.0(2)
C14 C8 C2 120.0(2)
C13 C9 C1 120.7(3)
C19 C10 C6 121.1(2)
C6 C12 C15 121.1(2)
C9 C13 C18 122.0(3)
C8 C14 C3 121.2(2)
C17 C15 C12 118.8(2)
C18 C16 C3 119.6(2)
C15 C17 C19 121.5(2)
C15 C17 Cl1 119.4(2)
C19 C17 Cl1 119.16(19)
C16 C18 C13 120.0(2)
C17 C19 C10 119.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C17 1.740(3)
C1 C9 1.399(3)
C1 C3 1.419(3)
C1 C4 1.448(3)
C2 C4 1.365(3)
C2 C8 1.436(3)
C2 C5 1.503(3)
C3 C14 1.408(3)
C3 C16 1.428(3)
C4 C11 1.486(3)
C5 O1 1.221(3)
C5 C6 1.497(3)
C6 C12 1.380(3)
C6 C10 1.389(3)
C8 C14 1.349(3)
C9 C13 1.351(4)
C10 C19 1.372(4)
C12 C15 1.382(3)
C13 C18 1.380(4)
C15 C17 1.370(3)
C16 C18 1.368(4)
C17 C19 1.371(4)
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2022-06-28T18:20:00+03:00
;
 Removed the '_chemical_name_systematic' data item that had an incorrect value.
;
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328713
