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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/71/7107165.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_7107165
loop_
_publ_author_name
'Feijun Wang'
'Mingliang Qu'
'Feng Chen'
'Li Li'
'Min Shi'
_publ_section_title
;
 An unusual Me3SiI-promoted [4+2] annulation and reduction: an efficient
 approach to construct 4H-benzopyrans
;
_journal_name_full               Chem.Commun.
_journal_page_first              437
_journal_paper_doi               10.1039/c1cc16028a
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C14 H13 Br O3'
_chemical_formula_weight         309.15
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.902(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.081(4)
_cell_length_b                   20.421(9)
_cell_length_c                   6.813(3)
_cell_measurement_reflns_used    2266
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      29.07
_cell_measurement_theta_min      2.46
_cell_volume                     1261.8(10)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2207
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.255
_exptl_absorpt_correction_T_max  0.5622
_exptl_absorpt_correction_T_min  0.4626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   twinabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         2.091
_refine_diff_density_min         -1.318
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0850P)²+1.9706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1586
_reflns_number_gt                1802
_reflns_number_total             2207
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc16028a.txt
_cod_data_source_block           dm11275
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7107165
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 1.35812(6) 0.39396(3) 0.79928(10) 0.0301(3) Uani 1 1 d .
C1 C 1.1641(6) 0.3575(3) 0.7804(9) 0.0212(12) Uani 1 1 d .
C2 C 1.1500(6) 0.2900(3) 0.7786(9) 0.0212(12) Uani 1 1 d .
H2 H 1.2349 0.2628 0.7858 0.025 Uiso 1 1 calc R
C3 C 1.0098(6) 0.2628(3) 0.7661(8) 0.0183(12) Uani 1 1 d .
C4 C 0.9911(6) 0.1894(3) 0.7636(8) 0.0189(12) Uani 1 1 d .
H4A H 1.0385 0.1709 0.6481 0.023 Uiso 1 1 calc R
H4B H 1.0404 0.1704 0.8834 0.023 Uiso 1 1 calc R
C5 C 0.8304(6) 0.1712(3) 0.7547(8) 0.0196(12) Uani 1 1 d .
C6 C 0.7947(7) 0.1015(3) 0.7513(9) 0.0239(13) Uani 1 1 d .
C7 C 0.6325(6) 0.0823(3) 0.7366(11) 0.0348(16) Uani 1 1 d .
H7A H 0.6021 0.0748 0.5968 0.042 Uiso 1 1 calc R
H7B H 0.6200 0.0406 0.8078 0.042 Uiso 1 1 calc R
C8 C 0.5336(7) 0.1331(3) 0.8193(11) 0.0318(14) Uani 1 1 d .
H8A H 0.5524 0.1357 0.9635 0.038 Uiso 1 1 calc R
H8B H 0.4294 0.1202 0.7930 0.038 Uiso 1 1 calc R
C9 C 0.5598(6) 0.2004(3) 0.7281(9) 0.0240(13) Uani 1 1 d .
H9A H 0.5234 0.2005 0.5886 0.029 Uiso 1 1 calc R
H9B H 0.5052 0.2344 0.7985 0.029 Uiso 1 1 calc R
C10 C 0.7218(6) 0.2154(3) 0.7423(8) 0.0189(12) Uani 1 1 d .
C11 C 0.8892(6) 0.3039(3) 0.7535(8) 0.0177(11) Uani 1 1 d .
C12 C 0.9037(6) 0.3725(3) 0.7520(9) 0.0204(12) Uani 1 1 d .
C13 C 1.0456(6) 0.4002(3) 0.7656(8) 0.0192(12) Uani 1 1 d .
H13 H 1.0596 0.4462 0.7647 0.023 Uiso 1 1 calc R
C14 C 0.7895(7) 0.4778(3) 0.7422(10) 0.0297(14) Uani 1 1 d .
H14A H 0.8434 0.4919 0.8631 0.045 Uiso 1 1 calc R
H14B H 0.6911 0.4976 0.7354 0.045 Uiso 1 1 calc R
H14C H 0.8433 0.4917 0.6282 0.045 Uiso 1 1 calc R
O1 O 0.7438(4) 0.28158(18) 0.7403(6) 0.0218(9) Uani 1 1 d .
O2 O 0.8921(5) 0.05990(19) 0.7562(7) 0.0325(10) Uani 1 1 d .
O3 O 0.7759(4) 0.40788(18) 0.7418(7) 0.0264(10) Uani 1 1 d .
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C13 C1 C2 123.7(5)
C13 C1 Br1 118.1(4)
C2 C1 Br1 118.2(4)
C1 C2 C3 119.0(5)
C1 C2 H2 120.5
C3 C2 H2 120.5
C11 C3 C2 118.9(5)
C11 C3 C4 121.1(5)
C2 C3 C4 120.1(5)
C5 C4 C3 110.7(4)
C5 C4 H4A 109.5
C3 C4 H4A 109.5
C5 C4 H4B 109.5
C3 C4 H4B 109.5
H4A C4 H4B 108.1
C10 C5 C6 119.7(5)
C10 C5 C4 123.2(5)
C6 C5 C4 117.1(5)
O2 C6 C5 121.1(5)
O2 C6 C7 121.2(5)
C5 C6 C7 117.7(5)
C8 C7 C6 113.1(5)
C8 C7 H7A 108.9
C6 C7 H7A 108.9
C8 C7 H7B 108.9
C6 C7 H7B 108.9
H7A C7 H7B 107.8
C7 C8 C9 111.1(5)
C7 C8 H8A 109.4
C9 C8 H8A 109.4
C7 C8 H8B 109.4
C9 C8 H8B 109.4
H8A C8 H8B 108.0
C10 C9 C8 109.1(5)
C10 C9 H9A 109.9
C8 C9 H9A 109.9
C10 C9 H9B 109.9
C8 C9 H9B 109.9
H9A C9 H9B 108.3
C5 C10 O1 124.1(5)
C5 C10 C9 125.8(5)
O1 C10 C9 110.1(5)
C3 C11 O1 123.5(5)
C3 C11 C12 122.2(5)
O1 C11 C12 114.4(5)
O3 C12 C13 124.4(5)
O3 C12 C11 116.6(5)
C13 C12 C11 119.0(5)
C1 C13 C12 117.3(5)
C1 C13 H13 121.3
C12 C13 H13 121.3
O3 C14 H14A 109.5
O3 C14 H14B 109.5
H14A C14 H14B 109.5
O3 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C10 O1 C11 117.4(4)
C12 O3 C14 117.0(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.911(5)
C1 C13 1.384(8)
C1 C2 1.384(8)
C2 C3 1.388(8)
C2 H2 0.9500
C3 C11 1.379(8)
C3 C4 1.509(7)
C4 C5 1.504(7)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C10 1.336(8)
C5 C6 1.459(8)
C6 O2 1.226(7)
C6 C7 1.522(8)
C7 C8 1.501(9)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.532(8)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.501(8)
C9 H9A 0.9900
C9 H9B 0.9900
C10 O1 1.367(6)
C11 O1 1.395(6)
C11 C12 1.407(8)
C12 O3 1.365(7)
C12 C13 1.406(8)
C13 H13 0.9500
C14 O3 1.433(7)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139182247
