#------------------------------------------------------------------------------
#$Date: 2022-06-29 03:34:58 +0300 (Wed, 29 Jun 2022) $
#$Revision: 276375 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158743.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_7158743
loop_
_publ_author_name
'Suzuki, Itaru'
'Hamada, Yuya'
'Uji, Yuki'
'Shibata, Ikuya'
_publ_section_title
;
 Reductive Coupling of Allenoates with Aldehydes Catalyzed by Halogenotin
 Hydride
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01096H
_journal_year                    2022
_chemical_formula_moiety         'C14 H16 Br2 O3'
_chemical_formula_sum            'C14 H16 Br2 O3'
_chemical_formula_weight         392.09
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-15 deposited with the CCDC.	2022-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                93.2370(10)
_cell_angle_beta                 108.2430(10)
_cell_angle_gamma                115.398(2)
_cell_formula_units_Z            2
_cell_length_a                   8.81840(10)
_cell_length_b                   8.9121(2)
_cell_length_c                   11.45210(10)
_cell_measurement_reflns_used    5768
_cell_measurement_temperature    123
_cell_measurement_theta_max      73.6320
_cell_measurement_theta_min      4.1830
_cell_volume                     752.85(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  32.00   0.50    0.05    --  -42.80  18.00 -15.00   52
  2  ω      9.00 115.00   0.50    0.05    --   42.80  18.00 -15.00  212
  3  ω    117.00 143.00   0.50    0.05    --   76.50  18.00 -15.00   52
  4  ω     71.00  96.00   0.50    0.05    --   42.80 125.00 150.00   50
  5  ω    100.00 146.00   0.50    0.05    --   76.50 125.00  30.00   92
  6  ω     44.00  88.00   0.50    0.05    --   76.50 -18.00 175.00   88
  7  ω     40.00 115.00   0.50    0.05    --   76.50-125.00  90.00  150
  8  ω     -4.00  22.00   0.50    0.05    --   42.80 -18.00 175.00   52
  9  ω    -28.00  65.00   0.50    0.05    --   42.80 -57.00  30.00  186
 10  ω    -76.00 -33.00   0.50    0.05    --  -42.80  18.00 -15.00   86
 11  ω    -89.00 -64.00   0.50    0.05    --  -42.80 125.00-180.00   50
 12  ω   -128.00 -32.00   0.50    0.05    -- -106.00  57.00 -90.00  192
 13  ω   -102.00 -32.00   0.50    0.05    -- -106.00 125.00 -90.00  140
 14  ω   -113.00 -72.00   0.50    0.05    -- -106.00 125.00  30.00   82
 15  ω   -115.00 -38.00   0.50    0.05    -- -106.00 125.00  60.00  154
 16  ω    -93.00 -29.00   0.50    0.05    -- -106.00  37.00  90.00  128
 17  ω   -107.00 -82.00   0.50    0.05    -- -106.00 125.00 -60.00   50
 18  ω   -129.00 -37.00   0.50    0.05    -- -106.00  77.00 -90.00  184
 19  ω   -113.00 -84.00   0.50    0.05    -- -106.00 -19.00  30.00   58
 20  ω   -128.00 -98.00   0.50    0.05    -- -106.00  37.00  90.00   60
 21  ω   -125.00 -64.00   0.50    0.05    -- -106.00  57.00  90.00  122
 22  ω   -120.00 -53.00   0.50    0.05    --  -42.80 -18.00 175.00  134
 23  ω   -130.00 -27.00   0.50    0.05    -- -106.00  18.00 -15.00  206
 24  ω   -110.00 -84.00   0.50    0.05    -- -106.00 125.00-180.00   52
 25  ω   -123.00 -28.00   0.50    0.05    -- -106.00  37.00-180.00  190
 26  ω   -173.00-124.00   0.50    0.05    -- -106.00 -19.00  30.00   98
 27  ω   -177.00 -91.00   0.50    0.05    -- -106.00 -37.00 120.00  172
 28  ω   -176.00-116.00   0.50    0.05    -- -106.00 -18.00 175.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0290928000
_diffrn_orient_matrix_UB_12      0.1583645000
_diffrn_orient_matrix_UB_13      0.0061092000
_diffrn_orient_matrix_UB_21      -0.1668062000
_diffrn_orient_matrix_UB_22      -0.0981618000
_diffrn_orient_matrix_UB_23      0.0339741000
_diffrn_orient_matrix_UB_31      0.1216916000
_diffrn_orient_matrix_UB_32      0.0616973000
_diffrn_orient_matrix_UB_33      0.1411163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7529
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.985
_diffrn_reflns_theta_min         4.169
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.849
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent intense colourless'
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.178
_refine_diff_density_max         0.795
_refine_diff_density_min         -1.559
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0438P)²+0.9259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2852
_reflns_number_total             2963
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01096h2.cif
_cod_data_source_block           dibromo
_cod_original_cell_volume        752.85(2)
_cod_database_code               7158743
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H16 Br2 O3'
_chemical_oxdiff_usercomment     hexane/ether
_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.
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C4(H4), C9(H9)
2.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C00I(H00A,H00B,H00C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.432
_oxdiff_exptl_absorpt_empirical_full_min 0.648
loop_
_space_group_symop_operation_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_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
Br2 Br -0.27500(4) 0.29424(3) 0.47025(3) 0.02126(10) Uani 1 1 d . . . . .
Br1 Br -0.30629(4) -0.10377(4) 0.83646(3) 0.02503(11) Uani 1 1 d . . . . .
O1 O 0.4008(2) 0.5486(2) 0.83990(18) 0.0167(4) Uani 1 1 d . . . . .
H1 H 0.370500 0.593651 0.888731 0.025 Uiso 1 1 calc GR . . . .
O3 O 0.7208(2) 0.4843(2) 0.78598(17) 0.0175(4) Uani 1 1 d . . . . .
O2 O 0.6791(3) 0.3801(3) 0.95319(18) 0.0220(4) Uani 1 1 d . . . . .
C6 C -0.2581(3) 0.1155(3) 0.6669(2) 0.0158(5) Uani 1 1 d . . . . .
H6 H -0.386535 0.059649 0.630047 0.019 Uiso 1 1 calc R . . . .
C5 C -0.1670(4) 0.0747(3) 0.7718(2) 0.0162(5) Uani 1 1 d . . . . .
C7 C -0.1546(3) 0.2410(3) 0.6178(2) 0.0145(5) Uani 1 1 d . . . . .
C8 C 0.0329(3) 0.3249(3) 0.6700(2) 0.0149(5) Uani 1 1 d . . . . .
H8 H 0.100363 0.410709 0.634387 0.018 Uiso 1 1 calc R . . . .
C3 C 0.1208(3) 0.2811(3) 0.7760(2) 0.0137(5) Uani 1 1 d . . . . .
C2 C 0.3263(3) 0.3697(3) 0.8355(2) 0.0146(5) Uani 1 1 d . . . . .
H2 H 0.362758 0.353419 0.923776 0.017 Uiso 1 1 calc R . . . .
C4 C 0.0200(3) 0.1550(3) 0.8275(2) 0.0153(5) Uani 1 1 d . . . . .
H4 H 0.078882 0.124675 0.899710 0.018 Uiso 1 1 calc R . . . .
C11 C 0.6176(3) 0.3921(3) 0.8449(2) 0.0160(5) Uani 1 1 d . . . . .
C1 C 0.4147(3) 0.3000(3) 0.7638(3) 0.0177(5) Uani 1 1 d . . . . .
C13 C 1.0045(4) 0.6924(4) 0.7855(3) 0.0263(6) Uani 1 1 d . . . . .
H13A H 0.975757 0.627319 0.702739 0.039 Uiso 1 1 calc GR . . . .
H13B H 1.135972 0.751666 0.831250 0.039 Uiso 1 1 calc GR . . . .
H13C H 0.959632 0.776027 0.774346 0.039 Uiso 1 1 calc GR . . . .
C12 C 0.9159(3) 0.5731(4) 0.8594(3) 0.0204(5) Uani 1 1 d . . . . .
H12A H 0.962946 0.490133 0.873535 0.024 Uiso 1 1 calc R . . . .
H12B H 0.941413 0.637805 0.942463 0.024 Uiso 1 1 calc R . . . .
C9 C 0.3800(4) 0.3359(4) 0.6340(3) 0.0254(6) Uani 1 1 d . . . . .
H9 H 0.431693 0.452175 0.628904 0.030 Uiso 1 1 calc R . . . .
C00I C 0.3471(4) 0.1093(4) 0.7640(3) 0.0284(7) Uani 1 1 d . . . . .
H00A H 0.370403 0.094381 0.850897 0.043 Uiso 1 1 calc GR . . . .
H00B H 0.411114 0.066573 0.726942 0.043 Uiso 1 1 calc GR . . . .
H00C H 0.216840 0.045857 0.714371 0.043 Uiso 1 1 calc GR . . . .
C10 C 0.2842(5) 0.2209(6) 0.5259(3) 0.0458(10) Uani 1 1 d . . . . .
H10A H 0.229802 0.103019 0.526140 0.055 Uiso 1 1 calc R . . . .
H10B H 0.269781 0.256279 0.448229 0.055 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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 7 0.0757
-5 0 2 0.1079
0 0 -7 0.0993
5 0 -2 0.1032
1 -3 6 0.0668
-1 -5 0 0.1235
0 5 -1 0.0469
5 -4 -3 0.1297
-6 4 2 0.1105
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
C11 O3 C12 115.8(2) . . ?
C7 C6 C5 117.4(2) . . ?
C6 C5 Br1 118.06(19) . . ?
C6 C5 C4 122.4(2) . . ?
C4 C5 Br1 119.6(2) . . ?
C6 C7 Br2 118.44(19) . . ?
C6 C7 C8 122.5(2) . . ?
C8 C7 Br2 119.05(19) . . ?
C7 C8 C3 118.8(2) . . ?
C8 C3 C2 120.3(2) . . ?
C4 C3 C8 120.0(2) . . ?
C4 C3 C2 119.6(2) . . ?
O1 C2 C3 111.3(2) . . ?
O1 C2 C1 106.8(2) . . ?
C3 C2 C1 113.5(2) . . ?
C5 C4 C3 119.0(2) . . ?
O3 C11 C1 113.9(2) . . ?
O2 C11 O3 123.0(2) . . ?
O2 C11 C1 123.1(2) . . ?
C11 C1 C2 105.3(2) . . ?
C11 C1 C00I 106.8(2) . . ?
C9 C1 C2 111.1(2) . . ?
C9 C1 C11 111.1(2) . . ?
C9 C1 C00I 113.6(2) . . ?
C00I C1 C2 108.6(2) . . ?
O3 C12 C13 107.5(2) . . ?
C10 C9 C1 126.2(3) . . ?
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
Br2 C7 1.900(3) . ?
Br1 C5 1.901(3) . ?
O1 C2 1.431(3) . ?
O3 C11 1.328(3) . ?
O3 C12 1.464(3) . ?
O2 C11 1.219(3) . ?
C6 C5 1.384(4) . ?
C6 C7 1.384(4) . ?
C5 C4 1.385(4) . ?
C7 C8 1.385(4) . ?
C8 C3 1.397(4) . ?
C3 C2 1.520(3) . ?
C3 C4 1.396(4) . ?
C2 C1 1.558(3) . ?
C11 C1 1.533(4) . ?
C1 C9 1.503(4) . ?
C1 C00I 1.541(4) . ?
C13 C12 1.504(4) . ?
C9 C10 1.325(5) . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.7992 0.1292 7.2001 0.0877 0.3653 0.9268
-5.3020 0.3444 2.4127 0.2235 0.9326 -0.2835
0.1068 -0.0845 -6.9140 -0.0587 -0.2444 -0.9679
5.2559 -0.3345 -1.7821 -0.2168 -0.9044 0.3675
0.9355 -2.8882 6.3169 -0.4460 0.3421 0.8271
-0.6421 -4.6691 -0.3307 -0.7228 0.5542 -0.4129
0.3502 5.0564 -1.3308 0.7824 -0.6000 0.1668
5.3856 -3.6803 -3.3008 -0.7597 -0.6492 -0.0375
-5.5733 3.5890 1.6357 0.7405 0.6329 -0.2260
