#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:42:53 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/97/7159770.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_7159770
loop_
_publ_author_name
'Jamis-Oliva, Omar'
'López, Roger'
'Galdámez, Antonio'
'Gallardo-Fuentes, Sebastián'
'Vilches-Herrera, Marcelo'
_publ_section_title
;
 Non-covalent interactions in the diastereoselective synthesis of
 cis-2,3-dihydrobenzofurans: experimental and computational studies
;
_journal_issue                   7
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              1441
_journal_page_last               1446
_journal_paper_doi               10.1039/D3OB02070C
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C15 H15 Br O4'
_chemical_formula_sum            'C15 H15 Br O4'
_chemical_formula_weight         339.18
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-08-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-10-11 deposited with the CCDC.	2024-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.990(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7333(3)
_cell_length_b                   15.4063(8)
_cell_length_c                   16.4742(9)
_cell_measurement_reflns_used    6626
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.628
_cell_measurement_theta_min      2.644
_cell_volume                     1451.62(13)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.798
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.1063
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.798
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36318
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.798
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         38.028
_diffrn_reflns_theta_min         1.812
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.841
_exptl_absorpt_correction_T_max  0.4990
_exptl_absorpt_correction_T_min  0.2969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1142 before and 0.0443 after correction.
The Ratio of minimum to maximum transmission is 0.5950.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_description       Polyhedron
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         6307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.2107
_refine_ls_R_factor_gt           0.0688
_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)+(0.0530P)²+1.0254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1577
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2606
_reflns_number_total             6307
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob02070c2.cif
_cod_data_source_block           scd23_133_0m
_cod_depositor_comments          'Adding full bibliography for 7159770.cif.'
_cod_database_code               7159770
_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   0.873
_shelx_estimated_absorpt_t_min   0.455
_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:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
;
_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 0.72326(8) 0.15283(3) 0.00780(2) 0.07829(19) Uani 1 1 d . . . . .
O1 O 0.2733(3) 0.04732(12) -0.31438(11) 0.0420(4) Uani 1 1 d . . . . .
O2 O 0.1892(3) 0.12596(17) -0.61239(13) 0.0590(6) Uani 1 1 d . . . . .
O3 O -0.1546(3) 0.14804(14) -0.56093(13) 0.0538(5) Uani 1 1 d . . . . .
O4 O 0.9940(4) 0.24588(16) -0.29396(15) 0.0641(6) Uani 1 1 d . . . . .
C1 C 0.5764(5) 0.11757(19) -0.09354(17) 0.0460(7) Uani 1 1 d . . . . .
C2 C 0.3627(6) 0.0761(2) -0.09490(18) 0.0513(7) Uani 1 1 d . . . . .
H2 H 0.292957 0.065482 -0.046573 0.062 Uiso 1 1 calc R U . . .
C3 C 0.2532(5) 0.05051(19) -0.16801(18) 0.0477(7) Uani 1 1 d . . . . .
H3 H 0.109861 0.022056 -0.170030 0.057 Uiso 1 1 calc R U . . .
C4 C 0.3616(4) 0.06820(16) -0.23781(16) 0.0356(6) Uani 1 1 d . . . . .
C5 C 0.5746(4) 0.11037(16) -0.23671(15) 0.0321(5) Uani 1 1 d . . . . .
C6 C 0.6845(5) 0.13609(17) -0.16376(16) 0.0400(6) Uani 1 1 d . . . . .
H6 H 0.827152 0.165026 -0.161849 0.048 Uiso 1 1 calc R U . . .
C7 C 0.6381(4) 0.12273(17) -0.32310(15) 0.0335(5) Uani 1 1 d . . . . .
H7 H 0.795(5) 0.1095(17) -0.3279(15) 0.030(6) Uiso 1 1 d . . . . .
C8 C 0.4634(4) 0.05919(18) -0.36784(16) 0.0374(6) Uani 1 1 d . . . . .
H8 H 0.538(4) 0.0027(19) -0.3707(16) 0.037(7) Uiso 1 1 d . . . . .
C9 C 0.3683(4) 0.08480(17) -0.45006(15) 0.0365(6) Uani 1 1 d . . . . .
H9 H 0.474664 0.090830 -0.489822 0.044 Uiso 1 1 calc R U . . .
C10 C 0.1481(4) 0.09979(19) -0.47204(17) 0.0427(6) Uani 1 1 d . . . . .
H10 H 0.037552 0.094341 -0.433621 0.051 Uiso 1 1 calc R U . . .
C11 C 0.0702(4) 0.12503(19) -0.55583(17) 0.0410(6) Uani 1 1 d . . . . .
C12 C -0.2507(5) 0.1757(2) -0.6401(2) 0.0556(8) Uani 1 1 d . . . . .
H12A H -0.219420 0.132407 -0.679817 0.083 Uiso 1 1 calc R U . . .
H12B H -0.179945 0.229594 -0.654223 0.083 Uiso 1 1 calc R U . . .
H12C H -0.416527 0.183443 -0.638823 0.083 Uiso 1 1 calc R U . . .
C13 C 0.6100(4) 0.21693(17) -0.35010(16) 0.0382(6) Uani 1 1 d . . . . .
H13A H 0.598581 0.219001 -0.409096 0.046 Uiso 1 1 calc R U . . .
H13B H 0.464760 0.239301 -0.331588 0.046 Uiso 1 1 calc R U . . .
C14 C 0.8079(5) 0.27507(19) -0.31856(16) 0.0422(6) Uani 1 1 d . . . . .
C15 C 0.7636(7) 0.3699(2) -0.3212(2) 0.0656(9) Uani 1 1 d . . . . .
H15A H 0.675514 0.384379 -0.371084 0.098 Uiso 1 1 calc R U . . .
H15B H 0.909926 0.400394 -0.318417 0.098 Uiso 1 1 calc R U . . .
H15C H 0.676590 0.386276 -0.275916 0.098 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_
_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
C4 O1 C8 106.49(18) . . ?
C11 O3 C12 116.2(2) . . ?
C2 C1 Br1 119.1(2) . . ?
C6 C1 Br1 118.7(2) . . ?
C6 C1 C2 122.1(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.1(3) . . ?
C4 C3 H3 121.0 . . ?
O1 C4 C3 124.6(2) . . ?
O1 C4 C5 113.2(2) . . ?
C3 C4 C5 122.3(2) . . ?
C4 C5 C7 108.6(2) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 C7 131.5(2) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 C1 117.9(3) . . ?
C5 C6 H6 121.1 . . ?
C5 C7 H7 110.6(15) . . ?
C5 C7 C8 100.3(2) . . ?
C5 C7 C13 111.7(2) . . ?
C8 C7 H7 114.7(16) . . ?
C13 C7 H7 105.5(16) . . ?
C13 C7 C8 114.3(2) . . ?
O1 C8 C7 106.1(2) . . ?
O1 C8 H8 105.6(16) . . ?
O1 C8 C9 110.1(2) . . ?
C7 C8 H8 108.3(15) . . ?
C9 C8 C7 116.9(2) . . ?
C9 C8 H8 109.3(16) . . ?
C8 C9 H9 117.0 . . ?
C10 C9 C8 126.0(2) . . ?
C10 C9 H9 117.0 . . ?
C9 C10 H10 119.0 . . ?
C9 C10 C11 121.9(2) . . ?
C11 C10 H10 119.0 . . ?
O2 C11 O3 123.4(3) . . ?
O2 C11 C10 125.6(2) . . ?
O3 C11 C10 111.0(2) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 108.8 . . ?
C7 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C7 113.8(2) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
O4 C14 C13 121.5(3) . . ?
O4 C14 C15 121.7(3) . . ?
C15 C14 C13 116.8(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 1.896(3) . ?
O1 C4 1.364(3) . ?
O1 C8 1.460(3) . ?
O2 C11 1.193(3) . ?
O3 C11 1.334(3) . ?
O3 C12 1.444(4) . ?
O4 C14 1.202(3) . ?
C1 C2 1.380(4) . ?
C1 C6 1.380(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(4) . ?
C4 C5 1.382(3) . ?
C5 C6 1.376(4) . ?
C5 C7 1.506(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.93(3) . ?
C7 C8 1.550(4) . ?
C7 C13 1.523(4) . ?
C8 H8 0.97(3) . ?
C8 C9 1.478(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.310(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.473(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.509(4) . ?
C14 C15 1.483(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
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
Br1 C1 C2 C3 179.6(2) . . . . ?
Br1 C1 C6 C5 -179.66(19) . . . . ?
O1 C4 C5 C6 179.5(2) . . . . ?
O1 C4 C5 C7 2.0(3) . . . . ?
O1 C8 C9 C10 3.6(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C1 C6 C5 -1.2(4) . . . . ?
C2 C3 C4 O1 -179.5(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C3 C4 C5 C7 -177.6(2) . . . . ?
C4 O1 C8 C7 -22.2(3) . . . . ?
C4 O1 C8 C9 -149.5(2) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C4 C5 C7 C8 -14.9(3) . . . . ?
C4 C5 C7 C13 106.6(2) . . . . ?
C5 C7 C8 O1 22.1(2) . . . . ?
C5 C7 C8 C9 145.3(2) . . . . ?
C5 C7 C13 C14 78.2(3) . . . . ?
C6 C1 C2 C3 1.2(5) . . . . ?
C6 C5 C7 C8 168.0(3) . . . . ?
C6 C5 C7 C13 -70.6(3) . . . . ?
C7 C5 C6 C1 177.5(3) . . . . ?
C7 C8 C9 C10 -117.5(3) . . . . ?
C7 C13 C14 O4 18.7(4) . . . . ?
C7 C13 C14 C15 -162.7(3) . . . . ?
C8 O1 C4 C3 -167.4(3) . . . . ?
C8 O1 C4 C5 13.1(3) . . . . ?
C8 C7 C13 C14 -168.8(2) . . . . ?
C8 C9 C10 C11 -179.9(3) . . . . ?
C9 C10 C11 O2 7.8(5) . . . . ?
C9 C10 C11 O3 -171.6(3) . . . . ?
C12 O3 C11 O2 -0.5(4) . . . . ?
C12 O3 C11 C10 179.0(3) . . . . ?
C13 C7 C8 O1 -97.4(2) . . . . ?
C13 C7 C8 C9 25.7(3) . . . . ?
