#------------------------------------------------------------------------------
#$Date: 2019-11-17 15:16:23 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230797 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/60/7156065.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_7156065
loop_
_publ_author_name
'Chehal, Navneet K.'
'Budzelaar, Peter H. M.'
'Hultin, Philip G.'
_publ_section_title
;
 E-Z isomerization in Suzuki cross-couplings of haloenones: ligand effects
 and evidence for a separate catalytic cycle.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1134
_journal_page_last               1143
_journal_paper_doi               10.1039/c7ob02925j
_journal_volume                  16
_journal_year                    2018
_chemical_formula_sum            'C16 H13 Cl O'
_chemical_formula_weight         256.71
_chemical_name_systematic
;
(Z)-2-chloro-3-(4-methylphenyl)-1-phenylprop-2-en-1-one
;
_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_Hall  '-P 2ac 2ab'
_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
_audit_update_record
;
2017-11-18 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   8.8054(8)
_cell_length_b                   11.6093(11)
_cell_length_c                   26.7629(15)
_cell_measurement_reflns_used    9816
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.22
_cell_measurement_theta_min      2.77
_cell_volume                     2735.8(4)
_computing_cell_refinement       'APEX2 software suite'
_computing_data_collection       'APEX2 software suite'
_computing_data_reduction        'APEX2 software suite'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker D8 three-circle diffractometer with an APEX-II CCD detector
;
_diffrn_measurement_method       'area detector φ and ω scan'
_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  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0088
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18840
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_correction_T_min  0.9344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular fragment'
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0202(16)
_refine_ls_extinction_expression
;
Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
;
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[σ²(Fo²)+(0.0599P)²+0.6839P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1132
_reflns_number_gt                2317
_reflns_number_total             2543
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob02925j2.cif
_cod_data_source_block           NV1b
_cod_depositor_comments
'Adding full bibliography for 7156061--7156066.cif.'
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7156065
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
C1 C 0.39517(16) 0.57592(11) 0.44156(5) 0.0443(3) Uani 1 1 d .
H1 H 0.4782 0.6056 0.4244 0.053 Uiso 1 1 calc R
C2 C 0.31254(16) 0.50338(12) 0.41382(5) 0.0483(3) Uani 1 1 d .
Cl2 Cl 0.15762(5) 0.42777(4) 0.43621(2) 0.0774(2) Uani 1 1 d .
C3 C 0.35310(17) 0.47362(13) 0.36142(6) 0.0537(4) Uani 1 1 d .
O3 O 0.31145(18) 0.38329(11) 0.34318(5) 0.0829(4) Uani 1 1 d .
C11 C 0.44300(17) 0.55611(13) 0.33059(5) 0.0504(4) Uani 1 1 d .
C12 C 0.41701(19) 0.67414(14) 0.33150(6) 0.0558(4) Uani 1 1 d .
H12 H 0.3504 0.7054 0.3548 0.067 Uiso 1 1 calc R
C13 C 0.4900(2) 0.74502(17) 0.29778(6) 0.0690(5) Uani 1 1 d .
H13 H 0.4706 0.8238 0.298 0.083 Uiso 1 1 calc R
C14 C 0.5916(2) 0.7000(2) 0.26371(6) 0.0781(6) Uani 1 1 d .
H14 H 0.641 0.7483 0.2413 0.094 Uiso 1 1 calc R
C15 C 0.6196(3) 0.5835(2) 0.26303(7) 0.0814(6) Uani 1 1 d .
H15 H 0.6891 0.5532 0.2404 0.098 Uiso 1 1 calc R
C16 C 0.5448(2) 0.51140(16) 0.29586(6) 0.0676(5) Uani 1 1 d .
H16 H 0.5626 0.4325 0.2948 0.081 Uiso 1 1 calc R
C21 C 0.38489(15) 0.61904(12) 0.49249(5) 0.0450(3) Uani 1 1 d .
C22 C 0.49035(19) 0.70280(13) 0.50574(6) 0.0563(4) Uani 1 1 d .
H22 H 0.5655 0.7231 0.483 0.068 Uiso 1 1 calc R
C23 C 0.4867(2) 0.75665(15) 0.55158(6) 0.0672(5) Uani 1 1 d .
H23 H 0.5588 0.8126 0.559 0.081 Uiso 1 1 calc R
C24 C 0.3779(2) 0.72896(16) 0.58658(6) 0.0653(5) Uani 1 1 d .
C25 C 0.2767(2) 0.64268(18) 0.57466(6) 0.0685(5) Uani 1 1 d .
H25 H 0.2049 0.6207 0.5983 0.082 Uiso 1 1 calc R
C26 C 0.27795(18) 0.58753(15) 0.52876(6) 0.0586(4) Uani 1 1 d .
H26 H 0.2079 0.5296 0.522 0.07 Uiso 1 1 calc R
C27 C 0.3707(3) 0.7935(2) 0.63575(8) 0.1003(8) Uani 1 1 d .
H271 H 0.3342 0.8703 0.63 0.15 Uiso 1 1 calc R
H272 H 0.4703 0.7968 0.6503 0.15 Uiso 1 1 calc R
H273 H 0.303 0.7543 0.6581 0.15 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 0.0 0.0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C2 C1 C21 134.64(13)
C1 C2 C3 122.59(13)
C1 C2 Cl2 123.79(11)
C3 C2 Cl2 113.47(11)
O3 C3 C2 120.48(15)
O3 C3 C11 119.53(14)
C2 C3 C11 119.98(12)
C12 C11 C16 119.05(15)
C12 C11 C3 122.42(14)
C16 C11 C3 118.15(15)
C13 C12 C11 119.99(15)
C12 C13 C14 120.53(18)
C15 C14 C13 119.84(18)
C14 C15 C16 120.15(18)
C15 C16 C11 120.42(18)
C22 C21 C26 117.06(14)
C22 C21 C1 115.96(12)
C26 C21 C1 126.95(14)
C23 C22 C21 121.93(15)
C22 C23 C24 121.04(17)
C25 C24 C23 117.51(15)
C25 C24 C27 122.23(19)
C23 C24 C27 120.3(2)
C24 C25 C26 122.41(16)
C25 C26 C21 119.93(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.338(2)
C1 C21 1.455(2)
C2 C3 1.488(2)
C2 Cl2 1.7293(14)
C3 O3 1.2134(19)
C3 C11 1.492(2)
C11 C12 1.389(2)
C11 C16 1.392(2)
C12 C13 1.380(2)
C13 C14 1.381(3)
C14 C15 1.375(3)
C15 C16 1.380(3)
C21 C22 1.391(2)
C21 C26 1.401(2)
C22 C23 1.377(2)
C23 C24 1.378(3)
C24 C25 1.378(3)
C24 C27 1.516(2)
C25 C26 1.385(2)
