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#$Date: 2023-06-26 11:24:54 +0300 (Mon, 26 Jun 2023) $
#$Revision: 284530 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/74/8107420.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_8107420
loop_
_publ_author_name
'Zhao, Wen-Ze'
_publ_section_title
;
 Crystal structure of 4-((6-bromohexyl)oxy)-2-hydroxybenzaldehyde,
 C13H17BrO3
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              293
_journal_page_last               294
_journal_paper_doi               10.1515/ncrs-2022-0598
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C13 H17 Br O3'
_chemical_formula_sum            'C13 H17 Br O3'
_chemical_formula_weight         301.17
_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   geom
_cell_angle_alpha                81.677(4)
_cell_angle_beta                 76.029(4)
_cell_angle_gamma                63.441(4)
_cell_formula_units_Z            2
_cell_length_a                   8.5759(12)
_cell_length_b                   9.1690(12)
_cell_length_c                   9.9698(12)
_cell_measurement_reflns_used    3744
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      25.19
_cell_measurement_theta_min      2.78
_cell_volume                     679.87(16)
_computing_cell_refinement       'SAINT (Brucker, 2012)[2]'
_computing_data_collection       'APEX2 (Brucker, 2012)[2]'
_computing_data_reduction        'SAINT (Brucker, 2012)[2]'
_computing_molecular_graphics    'Diamond 4.0[4]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)[1]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)[3]'
_diffrn_ambient_temperature      301.72
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13086
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.496
_diffrn_reflns_theta_min         2.486
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.018
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.9782
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0433
_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)+(0.0565P)²+0.2098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1253
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2187
_reflns_number_total             3382
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0598_suppl.cif
_cod_data_source_block           a
_cod_database_code               8107420
_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   0.713
_shelx_estimated_absorpt_t_min   0.660
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3A), C4(H4), C13(H13)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.87999(5) 0.03026(4) 1.35567(4) 0.0970(2) Uani 1 1 d . . . . .
O1 O 0.1199(3) 0.3067(3) 0.0987(2) 0.0873(6) Uani 1 1 d . . . . .
O2 O 0.3344(3) 0.4348(2) 0.62226(18) 0.0631(4) Uani 1 1 d . . . . .
O3 O 0.3084(3) 0.1328(2) 0.2870(2) 0.0803(6) Uani 1 1 d . . . . .
H3 H 0.2620 0.1479 0.2203 0.120 Uiso 1 1 calc GR . . . .
C1 C 0.0920(4) 0.4276(4) 0.1565(3) 0.0689(7) Uani 1 1 d . . . . .
H1 H 0.0212 0.5291 0.1207 0.083 Uiso 1 1 calc R . . . .
C2 C 0.1605(3) 0.4240(3) 0.2756(2) 0.0539(6) Uani 1 1 d . . . . .
C3 C 0.1202(3) 0.5702(3) 0.3340(3) 0.0578(6) Uani 1 1 d . . . . .
H3A H 0.0504 0.6689 0.2937 0.069 Uiso 1 1 calc R . . . .
C4 C 0.1802(3) 0.5712(3) 0.4475(3) 0.0560(6) Uani 1 1 d . . . . .
H4 H 0.1522 0.6693 0.4848 0.067 Uiso 1 1 calc R . . . .
C5 C 0.2849(3) 0.4225(3) 0.5077(2) 0.0519(5) Uani 1 1 d . . . . .
C6 C 0.4400(4) 0.2885(3) 0.6924(3) 0.0634(6) Uani 1 1 d . . . . .
H6A H 0.5511 0.2265 0.6310 0.076 Uiso 1 1 calc R . . . .
H6B H 0.3765 0.2209 0.7234 0.076 Uiso 1 1 calc R . . . .
C7 C 0.4751(4) 0.3403(3) 0.8139(3) 0.0576(6) Uani 1 1 d . . . . .
H7A H 0.3623 0.4038 0.8728 0.069 Uiso 1 1 calc R . . . .
H7B H 0.5354 0.4102 0.7807 0.069 Uiso 1 1 calc R . . . .
C8 C 0.5866(4) 0.1988(3) 0.8990(3) 0.0654(7) Uani 1 1 d . . . . .
H8A H 0.5222 0.1337 0.9393 0.079 Uiso 1 1 calc R . . . .
H8B H 0.6958 0.1301 0.8392 0.079 Uiso 1 1 calc R . . . .
C9 C 0.6315(4) 0.2556(3) 1.0125(3) 0.0603(6) Uani 1 1 d . . . . .
H9A H 0.5220 0.3332 1.0658 0.072 Uiso 1 1 calc R . . . .
H9B H 0.7042 0.3128 0.9708 0.072 Uiso 1 1 calc R . . . .
C10 C 0.7292(4) 0.1211(3) 1.1108(3) 0.0633(6) Uani 1 1 d . . . . .
H10A H 0.6557 0.0660 1.1568 0.076 Uiso 1 1 calc R . . . .
H10B H 0.8383 0.0415 1.0589 0.076 Uiso 1 1 calc R . . . .
C11 C 0.7718(4) 0.1905(4) 1.2160(3) 0.0699(7) Uani 1 1 d . . . . .
H11A H 0.6631 0.2771 1.2612 0.084 Uiso 1 1 calc R . . . .
H11B H 0.8521 0.2384 1.1693 0.084 Uiso 1 1 calc R . . . .
C12 C 0.2655(3) 0.2776(3) 0.3372(3) 0.0553(6) Uani 1 1 d . . . . .
C13 C 0.3292(3) 0.2758(3) 0.4522(3) 0.0569(6) Uani 1 1 d . . . . .
H13 H 0.4008 0.1775 0.4919 0.068 Uiso 1 1 calc R . . . .
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
C5 O2 C6 118.9(2) . .
C12 O3 H3 109.5 . .
O1 C1 H1 117.6 . .
O1 C1 C2 124.7(3) . .
C2 C1 H1 117.6 . .
C3 C2 C1 120.1(3) . .
C12 C2 C1 121.6(2) . .
C12 C2 C3 118.2(2) . .
C2 C3 H3A 119.1 . .
C4 C3 C2 121.7(2) . .
C4 C3 H3A 119.1 . .
C3 C4 H4 120.5 . .
C3 C4 C5 118.9(2) . .
C5 C4 H4 120.5 . .
O2 C5 C4 114.9(2) . .
O2 C5 C13 124.0(2) . .
C13 C5 C4 121.1(2) . .
O2 C6 H6A 110.4 . .
O2 C6 H6B 110.4 . .
O2 C6 C7 106.8(2) . .
H6A C6 H6B 108.6 . .
C7 C6 H6A 110.4 . .
C7 C6 H6B 110.4 . .
C6 C7 H7A 108.9 . .
C6 C7 H7B 108.9 . .
C6 C7 C8 113.4(2) . .
H7A C7 H7B 107.7 . .
C8 C7 H7A 108.9 . .
C8 C7 H7B 108.9 . .
C7 C8 H8A 109.3 . .
C7 C8 H8B 109.3 . .
H8A C8 H8B 107.9 . .
C9 C8 C7 111.8(2) . .
C9 C8 H8A 109.3 . .
C9 C8 H8B 109.3 . .
C8 C9 H9A 108.5 . .
C8 C9 H9B 108.5 . .
C8 C9 C10 115.0(2) . .
H9A C9 H9B 107.5 . .
C10 C9 H9A 108.5 . .
C10 C9 H9B 108.5 . .
C9 C10 H10A 109.6 . .
C9 C10 H10B 109.6 . .
H10A C10 H10B 108.1 . .
C11 C10 C9 110.3(2) . .
C11 C10 H10A 109.6 . .
C11 C10 H10B 109.6 . .
Br1 C11 H11A 108.9 . .
Br1 C11 H11B 108.9 . .
C10 C11 Br1 113.4(2) . .
C10 C11 H11A 108.9 . .
C10 C11 H11B 108.9 . .
H11A C11 H11B 107.7 . .
O3 C12 C2 121.4(2) . .
O3 C12 C13 117.6(2) . .
C13 C12 C2 121.1(2) . .
C5 C13 H13 120.5 . .
C12 C13 C5 119.0(2) . .
C12 C13 H13 120.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C11 1.942(3) .
O1 C1 1.224(4) .
O2 C5 1.346(3) .
O2 C6 1.434(3) .
O3 H3 0.8200 .
O3 C12 1.347(3) .
C1 H1 0.9300 .
C1 C2 1.437(4) .
C2 C3 1.403(4) .
C2 C12 1.392(4) .
C3 H3A 0.9300 .
C3 C4 1.355(4) .
C4 H4 0.9300 .
C4 C5 1.398(3) .
C5 C13 1.384(3) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C6 C7 1.502(4) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C7 C8 1.510(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C8 C9 1.504(4) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 C10 1.518(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C10 C11 1.492(4) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.379(4) .
C13 H13 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O1 0.82 1.92 2.641(3) 146.0 .
C11 H11B O1 0.97 2.56 3.495(4) 162.6 1_656
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
O1 C1 C2 C3 -180.0(3) . . . .
O1 C1 C2 C12 -0.9(4) . . . .
O2 C5 C13 C12 177.6(2) . . . .
O2 C6 C7 C8 -179.7(2) . . . .
O3 C12 C13 C5 -178.9(2) . . . .
C1 C2 C3 C4 178.9(2) . . . .
C1 C2 C12 O3 0.5(4) . . . .
C1 C2 C12 C13 -179.4(2) . . . .
C2 C3 C4 C5 0.0(4) . . . .
C2 C12 C13 C5 1.0(4) . . . .
C3 C2 C12 O3 179.6(2) . . . .
C3 C2 C12 C13 -0.3(4) . . . .
C3 C4 C5 O2 -178.2(2) . . . .
C3 C4 C5 C13 0.7(4) . . . .
C4 C5 C13 C12 -1.2(4) . . . .
C5 O2 C6 C7 179.6(2) . . . .
C6 O2 C5 C4 179.1(2) . . . .
C6 O2 C5 C13 0.2(4) . . . .
C6 C7 C8 C9 175.3(2) . . . .
C7 C8 C9 C10 174.7(2) . . . .
C8 C9 C10 C11 178.2(3) . . . .
C9 C10 C11 Br1 175.32(19) . . . .
C12 C2 C3 C4 -0.2(4) . . . .
