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#$Date: 2023-05-09 11:39:01 +0300 (Tue, 09 May 2023) $
#$Revision: 283620 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/71/8107147.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_8107147
loop_
_publ_author_name
'Yuan, Lin'
'Yuan, Xian-You'
'Li, Zhong-Yan'
'Zhang, Min'
_publ_section_title
;
 Crystal structure of 2-(2-bromophenyl)-5-ethyl-1,3-dioxane-5-carboxylic
 acid, C13H15BrO4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1209
_journal_page_last               1210
_journal_paper_doi               10.1515/ncrs-2016-0136
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C13 H15 Br O4'
_chemical_formula_sum            'C13 H15 Br O4'
_chemical_formula_weight         315.16
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.894(3)
_cell_length_b                   7.6064(16)
_cell_length_c                   21.571(4)
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      2.56
_cell_volume                     2607.9(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22782
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.18
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.156
_exptl_absorpt_correction_T_max  0.4613
_exptl_absorpt_correction_T_min  0.3801
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0268
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0358P)²+1.6290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0702
_reflns_number_gt                1970
_reflns_number_total             2276
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0136_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        2607.8(9)
_cod_database_code               8107147
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C2(H2A,H2B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C9(H9), C10(H10), C12(H12)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.073583(17) 0.12760(3) 0.338058(11) 0.05051(12) Uani 1 d . . .
O4 O 0.14606(9) 0.13521(17) 0.19368(6) 0.0327(3) Uani 1 d . . .
O3 O 0.07651(9) -0.08743(18) 0.14157(7) 0.0326(3) Uani 1 d . . .
C8 C 0.11771(12) -0.1296(2) 0.24636(9) 0.0283(4) Uani 1 d . . .
C13 C 0.11829(12) -0.0887(3) 0.30924(9) 0.0307(4) Uani 1 d . . .
O2 O -0.00822(9) 0.29548(19) 0.02122(7) 0.0412(4) Uani 1 d . . .
C11 C 0.17919(15) -0.3666(3) 0.33388(11) 0.0427(6) Uani 1 d . . .
H11 H 0.2000 -0.4455 0.3630 0.051 Uiso 1 calc . . R
C4 C 0.05808(13) 0.3237(3) 0.04761(9) 0.0302(4) Uani 1 d . . .
O1 O 0.09792(10) 0.4740(2) 0.04454(8) 0.0482(4) Uani 1 d . . .
H1 H 0.0703 0.5437 0.0240 0.072 Uiso 1 calc . . GR
C9 C 0.14818(13) -0.2935(3) 0.22891(10) 0.0349(5) Uani 1 d . . .
H9 H 0.1482 -0.3243 0.1872 0.042 Uiso 1 calc . . R
C5 C 0.11744(14) 0.2674(3) 0.15200(9) 0.0332(5) Uani 1 d . . .
H5A H 0.1591 0.3601 0.1491 0.040 Uiso 1 calc . . R
H5B H 0.0656 0.3184 0.1675 0.040 Uiso 1 calc . . R
C3 C 0.10215(12) 0.1879(3) 0.08747(9) 0.0280(4) Uani 1 d . . .
C2 C 0.18663(14) 0.1361(3) 0.05808(10) 0.0372(5) Uani 1 d . . .
H2A H 0.2233 0.2381 0.0586 0.045 Uiso 1 calc . . R
H2B H 0.2126 0.0466 0.0838 0.045 Uiso 1 calc . . R
C6 C 0.04309(13) 0.0299(3) 0.09604(9) 0.0322(4) Uani 1 d . . .
H6A H -0.0120 0.0707 0.1091 0.039 Uiso 1 calc . . R
H6B H 0.0367 -0.0315 0.0569 0.039 Uiso 1 calc . . R
C7 C 0.08622(12) -0.0016(3) 0.19868(9) 0.0295(4) Uani 1 d . . .
H7 H 0.0320 0.0469 0.2120 0.035 Uiso 1 calc . . R
C10 C 0.17844(14) -0.4120(3) 0.27221(11) 0.0409(5) Uani 1 d . . .
H10 H 0.1981 -0.5215 0.2597 0.049 Uiso 1 calc . . R
C12 C 0.14935(14) -0.2051(3) 0.35289(10) 0.0391(5) Uani 1 d . . .
H12 H 0.1501 -0.1747 0.3947 0.047 Uiso 1 calc . . R
C1 C 0.18201(18) 0.0676(4) -0.00749(12) 0.0609(7) Uani 1 d . . .
H1A H 0.1600 0.1576 -0.0342 0.091 Uiso 1 calc . . GR
H1B H 0.1457 -0.0333 -0.0088 0.091 Uiso 1 calc . . GR
H1C H 0.2373 0.0348 -0.0212 0.091 Uiso 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C7 O4 C5 110.67(15) . .
C7 O3 C6 110.71(15) . .
C13 C8 C7 121.65(18) . .
C9 C8 C13 117.53(18) . .
C9 C8 C7 120.82(18) . .
C8 C13 Br1 120.71(15) . .
C12 C13 Br1 117.75(16) . .
C12 C13 C8 121.5(2) . .
C10 C11 C12 120.6(2) . .
O2 C4 O1 123.32(19) . .
O2 C4 C3 123.06(19) . .
O1 C4 C3 113.61(17) . .
C10 C9 C8 121.5(2) . .
O4 C5 C3 110.17(16) . .
C4 C3 C5 108.58(16) . .
C4 C3 C2 110.16(16) . .
C4 C3 C6 108.61(16) . .
C2 C3 C5 109.66(17) . .
C6 C3 C5 107.18(16) . .
C6 C3 C2 112.53(17) . .
C1 C2 C3 115.64(19) . .
O3 C6 C3 110.13(15) . .
O4 C7 C8 107.77(15) . .
O3 C7 O4 110.46(16) . .
O3 C7 C8 109.64(16) . .
C11 C10 C9 119.5(2) . .
C11 C12 C13 119.4(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C13 1.897(2) .
O4 C5 1.423(2) .
O4 C7 1.414(2) .
O3 C6 1.429(2) .
O3 C7 1.403(2) .
C8 C13 1.392(3) .
C8 C9 1.389(3) .
C8 C7 1.502(3) .
C13 C12 1.384(3) .
O2 C4 1.217(2) .
C11 C10 1.374(3) .
C11 C12 1.379(3) .
C4 O1 1.309(3) .
C4 C3 1.515(3) .
C9 C10 1.384(3) .
C5 C3 1.537(3) .
C3 C2 1.536(3) .
C3 C6 1.536(3) .
C2 C1 1.509(3) .
