#------------------------------------------------------------------------------
#$Date: 2022-11-30 00:54:16 +0200 (Wed, 30 Nov 2022) $
#$Revision: 279628 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/10/7131048.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_7131048
loop_
_publ_author_name
'Ma, Ruize'
'Chen, Yang'
'Fang, Songjia'
'Jiang, Huanfeng'
'Yang, Shaorong'
'Wu, Wanqing'
_publ_section_title
;
 Palladium-catalyzed acetalization/cyclization of enynones with alcohols:
 rapid access to functionalized dihaloalkenyl dihydrofurans.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d2cc03949d
_journal_year                    2022
_chemical_formula_moiety         'C11 H14 Br2 O4'
_chemical_formula_sum            'C11 H14 Br2 O4'
_chemical_formula_weight         370.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-03 deposited with the CCDC.	2022-11-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.4480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5383(2)
_cell_length_b                   18.4779(5)
_cell_length_c                   11.2222(4)
_cell_measurement_reflns_used    6047
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.340
_cell_measurement_theta_min      2.861
_cell_volume                     1349.68(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14947
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.380
_diffrn_reflns_theta_min         2.204
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.006
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0835 before and 0.0478 after correction. The Ratio of minimum to maximum transmission is 0.6368. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0259
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0294P)²+0.5675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0608
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2260
_reflns_number_total             2754
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03949d2.cif
_cod_data_source_block           wyd_0m
_cod_original_cell_volume        1349.67(7)
_cod_database_code               7131048
_shelx_shelxl_version_number     2018/3
_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_max   0.558
_shelx_estimated_absorpt_t_min   0.315
_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
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C6(H6A,H6B,H6C), C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_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
Br1 Br 0.58073(4) 0.55814(2) 0.18834(3) 0.02730(9) Uani 1 1 d . . . . .
Br2 Br 0.14371(4) 0.62796(2) 0.22440(3) 0.03241(10) Uani 1 1 d . . . . .
O2 O 0.9220(3) 0.80920(10) 0.26104(17) 0.0252(4) Uani 1 1 d . . . . .
O1 O 0.7309(3) 0.70523(9) 0.28786(18) 0.0268(4) Uani 1 1 d . . . . .
O3 O 0.7105(3) 0.92870(11) 0.3895(2) 0.0459(6) Uani 1 1 d . . . . .
O4 O 1.1627(3) 0.86764(11) 0.0898(2) 0.0399(5) Uani 1 1 d . . . . .
C4 C 0.5808(4) 0.81430(14) 0.3382(2) 0.0226(6) Uani 1 1 d . . . . .
C2 C 0.5205(4) 0.69885(14) 0.2742(2) 0.0217(6) Uani 1 1 d . . . . .
C7 C 0.7889(4) 0.77741(14) 0.3352(3) 0.0240(6) Uani 1 1 d . . . . .
C1 C 0.4308(4) 0.63775(13) 0.2357(2) 0.0225(6) Uani 1 1 d . . . . .
C3 C 0.4302(4) 0.76727(14) 0.3054(2) 0.0234(6) Uani 1 1 d . . . . .
H3 H 0.287249 0.777078 0.302978 0.028 Uiso 1 1 calc R . . . .
C5 C 0.5591(4) 0.89082(14) 0.3748(3) 0.0254(6) Uani 1 1 d . . . . .
C8 C 0.9075(4) 0.76912(15) 0.4562(3) 0.0299(7) Uani 1 1 d . . . . .
H8A H 1.033441 0.741556 0.447955 0.045 Uiso 1 1 calc GR . . . .
H8B H 0.823056 0.743358 0.510060 0.045 Uiso 1 1 calc GR . . . .
H8C H 0.943225 0.817057 0.489265 0.045 Uiso 1 1 calc GR . . . .
C9 C 0.8466(4) 0.81799(16) 0.1387(3) 0.0311(7) Uani 1 1 d . . . . .
H9A H 0.696044 0.825613 0.132015 0.037 Uiso 1 1 calc R . . . .
H9B H 0.875331 0.773915 0.092987 0.037 Uiso 1 1 calc R . . . .
C6 C 0.3496(4) 0.91715(15) 0.3958(3) 0.0345(7) Uani 1 1 d . . . . .
H6A H 0.299596 0.890335 0.462560 0.052 Uiso 1 1 calc GR . . . .
H6B H 0.255827 0.909508 0.323410 0.052 Uiso 1 1 calc GR . . . .
H6C H 0.355743 0.968866 0.415109 0.052 Uiso 1 1 calc GR . . . .
C10 C 0.9500(5) 0.88197(16) 0.0887(3) 0.0346(7) Uani 1 1 d . . . . .
H10A H 0.890500 0.891337 0.005668 0.042 Uiso 1 1 calc R . . . .
H10B H 0.928220 0.925451 0.137424 0.042 Uiso 1 1 calc R . . . .
C11 C 1.2725(6) 0.92703(19) 0.0469(4) 0.0558(10) Uani 1 1 d . . . . .
H11A H 1.217118 0.938588 -0.035118 0.084 Uiso 1 1 calc GR . . . .
H11B H 1.418139 0.914305 0.047724 0.084 Uiso 1 1 calc GR . . . .
H11C H 1.258016 0.969177 0.098433 0.084 Uiso 1 1 calc GR . . . .
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'
Br Br -0.2901 2.4595 '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
C7 O2 C9 116.5(2) . . ?
C2 O1 C7 109.78(18) . . ?
C10 O4 C11 112.4(2) . . ?
C3 C4 C7 109.8(2) . . ?
C3 C4 C5 127.4(2) . . ?
C5 C4 C7 122.8(2) . . ?
O1 C2 C3 108.9(2) . . ?
C1 C2 O1 121.1(2) . . ?
C1 C2 C3 130.0(2) . . ?
O2 C7 O1 108.7(2) . . ?
O2 C7 C4 115.8(2) . . ?
O2 C7 C8 106.5(2) . . ?
O1 C7 C4 102.32(19) . . ?
O1 C7 C8 109.0(2) . . ?
C8 C7 C4 114.2(2) . . ?
Br1 C1 Br2 116.87(13) . . ?
C2 C1 Br1 122.32(19) . . ?
C2 C1 Br2 120.80(19) . . ?
C4 C3 C2 109.1(2) . . ?
C4 C3 H3 125.5 . . ?
C2 C3 H3 125.5 . . ?
O3 C5 C4 119.4(2) . . ?
O3 C5 C6 122.7(2) . . ?
C4 C5 C6 117.9(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 H9A 109.9 . . ?
O2 C9 H9B 109.9 . . ?
O2 C9 C10 108.9(2) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O4 C10 C9 109.1(2) . . ?
O4 C10 H10A 109.9 . . ?
O4 C10 H10B 109.9 . . ?
C9 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
Br1 C1 1.872(2) . ?
Br2 C1 1.878(3) . ?
O2 C7 1.391(3) . ?
O2 C9 1.423(3) . ?
O1 C2 1.375(3) . ?
O1 C7 1.472(3) . ?
O3 C5 1.211(3) . ?
O4 C10 1.414(3) . ?
O4 C11 1.421(4) . ?
C4 C7 1.525(3) . ?
C4 C3 1.339(4) . ?
C4 C5 1.483(4) . ?
C2 C1 1.326(4) . ?
C2 C3 1.452(3) . ?
C7 C8 1.506(4) . ?
C3 H3 0.9500 . ?
C5 C6 1.494(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.497(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
