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#$Date: 2024-01-06 10:25:10 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288824 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/72/7247295.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_7247295
loop_
_publ_author_name
'Cioc, Răzvan C'
'Harsevoort, Eva'
'Lutz, Martin'
'Bruijnincx, Pieter C. A.'
_publ_section_title
;
 Efficient synthesis of fully renewable, furfural-derived building blocks
 via formal Diels-Alder cycloaddition of atypical addends.
;
_journal_issue                   23
_journal_name_full
'Green chemistry : an international journal and green chemistry resource : GC'
_journal_page_first              9689
_journal_page_last               9694
_journal_paper_doi               10.1039/d3gc02357e
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C11 H13 Br O3'
_chemical_formula_sum            'C11 H13 Br O3'
_chemical_formula_weight         273.12
_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   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-12-06 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                107.710(4)
_cell_angle_beta                 98.149(4)
_cell_angle_gamma                105.204(4)
_cell_formula_units_Z            2
_cell_length_a                   5.8474(4)
_cell_length_b                   9.4994(5)
_cell_length_c                   11.3086(6)
_cell_measurement_reflns_used    8217
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      1.94
_cell_volume                     560.43(6)
_computing_cell_refinement       Peakref
_computing_data_collection       Apex3
_computing_data_reduction        'Eval15, Sadabs'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9421
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         1.948
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    3.652
_exptl_absorpt_correction_T_max  0.7186
_exptl_absorpt_correction_T_min  0.3673
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0240
_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)+(0.0348P)²+0.1683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0622
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2363
_reflns_number_total             2576
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc02357e2.cif
_cod_data_source_block           l1229a
_cod_depositor_comments
'Adding full bibliography for 7247295--7247296.cif.'
_cod_original_cell_volume        560.42(6)
_cod_database_code               7247295
_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.
;
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
Br1 Br 0.32725(4) 0.73728(2) 0.04274(2) 0.03221(8) Uani 1 1 d . . . . .
O1 O 0.3781(2) 0.78981(13) 0.30113(11) 0.0205(2) Uani 1 1 d . . . . .
O2 O 0.2271(2) 0.68313(15) 0.50445(12) 0.0274(3) Uani 1 1 d . . . . .
O3 O 0.6415(2) 0.78976(14) 0.61004(11) 0.0223(2) Uani 1 1 d . . . . .
C1 C 0.4574(3) 0.7051(2) 0.19553(16) 0.0229(3) Uani 1 1 d . . . . .
C2 C 0.3570(4) 0.5353(2) 0.19207(18) 0.0281(4) Uani 1 1 d . . . . .
H2A H 0.181065 0.486785 0.149225 0.034 Uiso 1 1 calc R U . . .
H2B H 0.448803 0.469026 0.149762 0.034 Uiso 1 1 calc R U . . .
C3 C 0.4039(3) 0.56633(19) 0.33697(17) 0.0232(3) Uani 1 1 d . . . . .
H3 H 0.518237 0.513776 0.364037 0.028 Uiso 1 1 calc R U . . .
C4 C 0.1828(3) 0.5426(2) 0.39449(18) 0.0281(4) Uani 1 1 d . . . . .
H4A H 0.033492 0.524562 0.330663 0.034 Uiso 1 1 calc R U . . .
H4B H 0.160272 0.450872 0.421241 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4543(3) 0.79529(19) 0.52070(16) 0.0205(3) Uani 1 1 d . . . . .
H5 H 0.440760 0.902650 0.544598 0.025 Uiso 1 1 calc R U . . .
C6 C 0.5189(3) 0.74789(18) 0.39377(16) 0.0192(3) Uani 1 1 d . . . . .
C7 C 0.7707(3) 0.7929(2) 0.36973(18) 0.0267(4) Uani 1 1 d . . . . .
H7 H 0.923185 0.832202 0.430524 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7323(3) 0.7655(2) 0.24445(18) 0.0283(4) Uani 1 1 d . . . . .
H8 H 0.851469 0.780485 0.196453 0.034 Uiso 1 1 calc R U . . .
C9 C 0.6051(3) 0.8343(2) 0.73645(16) 0.0233(3) Uani 1 1 d . . . . .
H9A H 0.473005 0.749576 0.743375 0.028 Uiso 1 1 calc R U . . .
H9B H 0.555436 0.929159 0.755242 0.028 Uiso 1 1 calc R U . . .
C10 C 0.8352(3) 0.8659(2) 0.83075(17) 0.0259(4) Uani 1 1 d . . . . .
H10 H 0.826748 0.882970 0.917040 0.031 Uiso 1 1 calc R U . . .
C11 C 1.0486(3) 0.8722(2) 0.80448(18) 0.0296(4) Uani 1 1 d . . . . .
H11A H 1.065044 0.855779 0.719392 0.036 Uiso 1 1 calc R U . . .
H11B H 1.186373 0.893045 0.870567 0.036 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 0.0033 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_
_diffrn_orient_matrix_type
_diffrn_orient_matrix_UB_11
_diffrn_orient_matrix_UB_12
_diffrn_orient_matrix_UB_13
_diffrn_orient_matrix_UB_21
_diffrn_orient_matrix_UB_22
_diffrn_orient_matrix_UB_23
_diffrn_orient_matrix_UB_31
_diffrn_orient_matrix_UB_32
_diffrn_orient_matrix_UB_33
'Nonius RMAT' 0.1551054 0.0702485 0.0646267 -0.0095135 -0.0791556 0.0421966
0.0958920 -0.0494570 -0.0564811
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 C6 93.97(11) . . ?
C5 O2 C4 111.04(13) . . ?
C5 O3 C9 112.51(13) . . ?
O1 C1 C8 102.58(14) . . ?
O1 C1 C2 101.74(13) . . ?
C8 C1 C2 109.61(15) . . ?
O1 C1 Br1 109.84(11) . . ?
C8 C1 Br1 116.74(12) . . ?
C2 C1 Br1 114.58(12) . . ?
C3 C2 C1 99.77(13) . . ?
C3 C2 H2A 111.8 . . ?
C1 C2 H2A 111.8 . . ?
C3 C2 H2B 111.8 . . ?
C1 C2 H2B 111.8 . . ?
H2A C2 H2B 109.5 . . ?
C4 C3 C2 117.63(16) . . ?
C4 C3 C6 101.08(13) . . ?
C2 C3 C6 101.26(13) . . ?
C4 C3 H3 111.9 . . ?
C2 C3 H3 111.9 . . ?
C6 C3 H3 111.9 . . ?
O2 C4 C3 107.53(14) . . ?
O2 C4 H4A 110.2 . . ?
C3 C4 H4A 110.2 . . ?
O2 C4 H4B 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
O3 C5 O2 112.28(13) . . ?
O3 C5 C6 106.37(13) . . ?
O2 C5 C6 105.29(13) . . ?
O3 C5 H5 110.9 . . ?
O2 C5 H5 110.9 . . ?
C6 C5 H5 110.9 . . ?
O1 C6 C5 111.35(13) . . ?
O1 C6 C7 102.17(13) . . ?
C5 C6 C7 126.52(15) . . ?
O1 C6 C3 100.39(13) . . ?
C5 C6 C3 104.65(13) . . ?
C7 C6 C3 108.89(14) . . ?
C8 C7 C6 104.93(16) . . ?
C8 C7 H7 127.5 . . ?
C6 C7 H7 127.5 . . ?
C7 C8 C1 104.89(16) . . ?
C7 C8 H8 127.6 . . ?
C1 C8 H8 127.6 . . ?
O3 C9 C10 109.93(14) . . ?
O3 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
O3 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 C9 125.45(17) . . ?
C11 C10 H10 117.3 . . ?
C9 C10 H10 117.3 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
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 1.9308(17) . ?
O1 C1 1.434(2) . ?
O1 C6 1.4544(19) . ?
O2 C5 1.415(2) . ?
O2 C4 1.453(2) . ?
O3 C5 1.404(2) . ?
O3 C9 1.426(2) . ?
C1 C8 1.514(3) . ?
C1 C2 1.551(2) . ?
C2 C3 1.544(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.523(2) . ?
C3 C6 1.560(2) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.502(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.510(2) . ?
C7 C8 1.334(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.491(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.313(3) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9500 . ?
C11 H11B 0.9500 . ?
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
C6 O1 C1 C8 -51.53(14) . . . . ?
C6 O1 C1 C2 61.89(14) . . . . ?
C6 O1 C1 Br1 -176.32(11) . . . . ?
O1 C1 C2 C3 -38.38(16) . . . . ?
C8 C1 C2 C3 69.68(17) . . . . ?
Br1 C1 C2 C3 -156.83(12) . . . . ?
C1 C2 C3 C4 109.60(16) . . . . ?
C1 C2 C3 C6 0.60(17) . . . . ?
C5 O2 C4 C3 1.11(19) . . . . ?
C2 C3 C4 O2 -128.78(15) . . . . ?
C6 C3 C4 O2 -19.68(18) . . . . ?
C9 O3 C5 O2 -66.05(17) . . . . ?
C9 O3 C5 C6 179.28(13) . . . . ?
C4 O2 C5 O3 -96.25(16) . . . . ?
C4 O2 C5 C6 19.08(18) . . . . ?
C1 O1 C6 C5 -170.78(13) . . . . ?
C1 O1 C6 C7 51.67(14) . . . . ?
C1 O1 C6 C3 -60.43(13) . . . . ?
O3 C5 C6 O1 -164.19(12) . . . . ?
O2 C5 C6 O1 76.47(16) . . . . ?
O3 C5 C6 C7 -39.4(2) . . . . ?
O2 C5 C6 C7 -158.70(15) . . . . ?
O3 C5 C6 C3 88.22(15) . . . . ?
O2 C5 C6 C3 -31.12(16) . . . . ?
C4 C3 C6 O1 -84.90(15) . . . . ?
C2 C3 C6 O1 36.48(16) . . . . ?
C4 C3 C6 C5 30.60(17) . . . . ?
C2 C3 C6 C5 151.99(14) . . . . ?
C4 C3 C6 C7 168.29(14) . . . . ?
C2 C3 C6 C7 -70.32(17) . . . . ?
O1 C6 C7 C8 -33.55(18) . . . . ?
C5 C6 C7 C8 -162.10(16) . . . . ?
C3 C6 C7 C8 72.03(18) . . . . ?
C6 C7 C8 C1 0.30(19) . . . . ?
O1 C1 C8 C7 33.63(18) . . . . ?
C2 C1 C8 C7 -73.88(19) . . . . ?
Br1 C1 C8 C7 153.75(13) . . . . ?
C5 O3 C9 C10 -165.48(14) . . . . ?
O3 C9 C10 C11 8.2(3) . . . . ?
