#------------------------------------------------------------------------------
#$Date: 2020-08-06 16:03:13 +0300 (Thu, 06 Aug 2020) $
#$Revision: 254906 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/62/7126209.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_7126209
loop_
_publ_author_name
'Zhou, Pan'
'Xu, Tao'
_publ_section_title
;
 Nickel-catalyzed intramolecular desymmetrization addition of aryl halides
 to 1,3-diketones.
;
_journal_issue                   59
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8194
_journal_page_last               8197
_journal_paper_doi               10.1039/d0cc00457j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C14 H16 O2'
_chemical_formula_weight         216.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-09-05 deposited with the CCDC.	2020-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4235(5)
_cell_length_b                   10.6627(7)
_cell_length_c                   12.6898(8)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      58.03
_cell_measurement_theta_min      4.71
_cell_volume                     1139.76(12)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19374
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         58.095
_diffrn_reflns_theta_min         5.484
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
; 
 Refined as a perfect inversion twin. 
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0274
_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)+(0.0365P)²+0.1460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0721
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2332
_reflns_number_total             2419
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc00457j2.cif
_cod_data_source_block           ga_90423a_a
_cod_depositor_comments          'Adding full bibliography for 7126209.cif.'
_cod_database_code               7126209
_shelx_shelxl_version_number     2016/6
_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. 
;
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.983
loop_
_space_group_symop_operation_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'
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 0.65007(13) 0.39832(10) 0.35463(10) 0.0400(3) Uani 1 1 d . . . . .
H1 H 0.607(3) 0.378(2) 0.2988(18) 0.057(6) Uiso 1 1 d . . . . .
O2 O 0.44517(15) 0.82097(10) 0.35297(9) 0.0452(3) Uani 1 1 d . . . . .
C1 C 0.56077(16) 0.49882(13) 0.40078(11) 0.0295(3) Uani 1 1 d . . . . .
C2 C 0.63667(19) 0.51949(15) 0.50835(12) 0.0376(3) Uani 1 1 d . . . . .
H2A H 0.618442 0.446073 0.551830 0.045 Uiso 1 1 calc R U . . .
H2B H 0.750424 0.528982 0.499549 0.045 Uiso 1 1 calc R U . . .
C3 C 0.5717(2) 0.63402(16) 0.56436(12) 0.0412(4) Uani 1 1 d . . . . .
H3A H 0.624774 0.644059 0.631685 0.049 Uiso 1 1 calc R U . . .
H3B H 0.459186 0.622970 0.577559 0.049 Uiso 1 1 calc R U . . .
C4 C 0.5977(2) 0.75059(16) 0.49736(14) 0.0435(4) Uani 1 1 d . . . . .
H4A H 0.551217 0.822504 0.532598 0.052 Uiso 1 1 calc R U . . .
H4B H 0.710666 0.765751 0.490053 0.052 Uiso 1 1 calc R U . . .
C5 C 0.52477(17) 0.73693(14) 0.38987(11) 0.0320(3) Uani 1 1 d . . . . .
C6 C 0.56009(17) 0.61748(13) 0.32689(10) 0.0312(3) Uani 1 1 d . . . . .
C7 C 0.4218(2) 0.59070(14) 0.25022(11) 0.0372(3) Uani 1 1 d . . . . .
H7A H 0.373110 0.668006 0.226151 0.045 Uiso 1 1 calc R U . . .
H7B H 0.457823 0.543153 0.189605 0.045 Uiso 1 1 calc R U . . .
C8 C 0.30834(18) 0.51543(13) 0.31591(11) 0.0337(3) Uani 1 1 d . . . . .
C9 C 0.1481(2) 0.49097(16) 0.29981(14) 0.0445(4) Uani 1 1 d . . . . .
H9 H 0.095773 0.524459 0.241725 0.053 Uiso 1 1 calc R U . . .
C10 C 0.0671(2) 0.41644(18) 0.37089(15) 0.0510(4) Uani 1 1 d . . . . .
H10 H -0.040154 0.399956 0.360455 0.061 Uiso 1 1 calc R U . . .
C11 C 0.1441(2) 0.36612(18) 0.45738(15) 0.0494(4) Uani 1 1 d . . . . .
H11 H 0.088224 0.316203 0.504668 0.059 Uiso 1 1 calc R U . . .
C12 C 0.3045(2) 0.38969(15) 0.47407(12) 0.0404(3) Uani 1 1 d . . . . .
H12 H 0.356570 0.355533 0.531962 0.048 Uiso 1 1 calc R U . . .
C13 C 0.38540(16) 0.46485(13) 0.40308(11) 0.0308(3) Uani 1 1 d . . . . .
C14 C 0.7197(2) 0.64007(18) 0.27128(15) 0.0477(4) Uani 1 1 d . . . . .
H14A H 0.711283 0.712244 0.226405 0.072 Uiso 1 1 calc R U . . .
H14B H 0.746580 0.567941 0.229664 0.072 Uiso 1 1 calc R U . . .
H14C H 0.800878 0.654115 0.323043 0.072 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0389 0.0241 '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
C1 O1 H1 108.4(16) . . ?
O1 C1 C13 109.83(11) . . ?
O1 C1 C2 104.71(11) . . ?
C13 C1 C2 115.13(12) . . ?
O1 C1 C6 111.04(11) . . ?
C13 C1 C6 101.49(11) . . ?
C2 C1 C6 114.76(12) . . ?
C3 C2 C1 112.68(13) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 110.15(13) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 111.67(13) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
O2 C5 C4 120.30(14) . . ?
O2 C5 C6 121.32(13) . . ?
C4 C5 C6 118.33(13) . . ?
C5 C6 C14 106.19(13) . . ?
C5 C6 C7 109.62(12) . . ?
C14 C6 C7 113.54(12) . . ?
C5 C6 C1 110.97(10) . . ?
C14 C6 C1 113.32(12) . . ?
C7 C6 C1 103.26(11) . . ?
C8 C7 C6 103.26(11) . . ?
C8 C7 H7A 111.1 . . ?
C6 C7 H7A 111.1 . . ?
C8 C7 H7B 111.1 . . ?
C6 C7 H7B 111.1 . . ?
H7A C7 H7B 109.1 . . ?
C9 C8 C13 119.81(15) . . ?
C9 C8 C7 129.58(15) . . ?
C13 C8 C7 110.60(13) . . ?
C10 C9 C8 119.42(16) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.64(16) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 120.42(17) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 118.93(16) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C8 120.78(14) . . ?
C12 C13 C1 128.92(13) . . ?
C8 C13 C1 110.21(13) . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 C1 1.4342(17) . ?
O1 H1 0.82(2) . ?
O2 C5 1.2132(19) . ?
C1 C13 1.5213(19) . ?
C1 C2 1.5234(19) . ?
C1 C6 1.5748(19) . ?
C2 C3 1.515(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.522(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.503(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.5328(19) . ?
C6 C14 1.537(2) . ?
C6 C7 1.544(2) . ?
C7 C8 1.501(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.390(2) . ?
C8 C13 1.391(2) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(2) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82(2) 2.07(2) 2.8747(17) 166(2) 3_645
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 172.67(12) . . . . ?
C13 C1 C2 C3 -66.63(17) . . . . ?
C6 C1 C2 C3 50.67(17) . . . . ?
C1 C2 C3 C4 -58.31(18) . . . . ?
C2 C3 C4 C5 56.33(19) . . . . ?
C3 C4 C5 O2 133.60(16) . . . . ?
C3 C4 C5 C6 -49.2(2) . . . . ?
O2 C5 C6 C14 93.18(17) . . . . ?
C4 C5 C6 C14 -84.02(16) . . . . ?
O2 C5 C6 C7 -29.84(19) . . . . ?
C4 C5 C6 C7 152.95(13) . . . . ?
O2 C5 C6 C1 -143.25(14) . . . . ?
C4 C5 C6 C1 39.55(18) . . . . ?
O1 C1 C6 C5 -157.82(11) . . . . ?
C13 C1 C6 C5 85.49(13) . . . . ?
C2 C1 C6 C5 -39.33(16) . . . . ?
O1 C1 C6 C14 -38.45(16) . . . . ?
C13 C1 C6 C14 -155.13(13) . . . . ?
C2 C1 C6 C14 80.04(16) . . . . ?
O1 C1 C6 C7 84.81(13) . . . . ?
C13 C1 C6 C7 -31.87(13) . . . . ?
C2 C1 C6 C7 -156.69(12) . . . . ?
C5 C6 C7 C8 -87.14(13) . . . . ?
C14 C6 C7 C8 154.29(13) . . . . ?
C1 C6 C7 C8 31.17(14) . . . . ?
C6 C7 C8 C9 162.06(15) . . . . ?
C6 C7 C8 C13 -18.95(16) . . . . ?
C13 C8 C9 C10 0.0(2) . . . . ?
C7 C8 C9 C10 178.91(15) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C8 -0.5(2) . . . . ?
C11 C12 C13 C1 -176.59(15) . . . . ?
C9 C8 C13 C12 0.3(2) . . . . ?
C7 C8 C13 C12 -178.80(13) . . . . ?
C9 C8 C13 C1 177.07(13) . . . . ?
C7 C8 C13 C1 -2.03(16) . . . . ?
O1 C1 C13 C12 80.43(18) . . . . ?
C2 C1 C13 C12 -37.4(2) . . . . ?
C6 C1 C13 C12 -162.01(15) . . . . ?
O1 C1 C13 C8 -96.01(13) . . . . ?
C2 C1 C13 C8 146.13(13) . . . . ?
C6 C1 C13 C8 21.56(14) . . . . ?
