#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/70/2227063.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2227063
loop_
_publ_author_name
'Shi, Yong-Heng'
'Zhao, Gui-Long'
'Shao, Hua'
'Liu, Wei'
'Xu, Wei-Ren'
_publ_section_title
;
 (5-Bromo-2-methylphenyl)(4-ethoxyphenyl)methanone
;
_journal_coeditor_code           RZ2475
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2038
_journal_paper_doi               10.1107/S1600536810027327
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H15 Br O2'
_chemical_formula_moiety         'C16 H15 Br O2'
_chemical_formula_sum            'C16 H15 Br O2'
_chemical_formula_weight         319.19
_chemical_name_systematic
;
(5-Bromo-2-methylphenyl)(4-ethoxyphenyl)methanone
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.5730(19)
_cell_length_b                   13.188(3)
_cell_length_c                   22.205(4)
_cell_measurement_reflns_used    6268
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.863
_cell_measurement_theta_min      2.128
_cell_volume                     2803.4(10)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17506
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.927
_exptl_absorpt_correction_T_max  0.6516
_exptl_absorpt_correction_T_min  0.4738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(crystalclear; Rigaku, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.844
_refine_diff_density_min         -0.568
_refine_ls_extinction_coef       0.0120(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0598P)²+1.3319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                2133
_reflns_number_total             2479
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2475.cif
_cod_data_source_block           I
_cod_database_code               2227063
_cod_database_fobs_code          2227063
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 -0.00393(3) 0.34535(2) 0.307507(13) 0.03274(18) Uani d . 1 . .
O O1 0.0807(2) 0.03567(15) 0.10091(9) 0.0353(5) Uani d . 1 . .
O O2 0.1222(2) 0.43270(15) -0.05895(8) 0.0322(5) Uani d . 1 . .
C C1 0.3438(3) 0.0117(2) 0.18087(13) 0.0354(7) Uani d . 1 . .
H H1A 0.4351 0.0104 0.2009 0.053 Uiso calc R 1 . .
H H1B 0.3562 0.0299 0.1384 0.053 Uiso calc R 1 . .
H H1C 0.3005 -0.0555 0.1836 0.053 Uiso calc R 1 . .
C C2 0.2512(3) 0.08893(19) 0.21113(13) 0.0259(6) Uani d . 1 . .
C C3 0.2670(3) 0.1078(2) 0.27228(13) 0.0286(6) Uani d . 1 . .
H H3 0.3328 0.0691 0.2946 0.034 Uiso calc R 1 . .
C C4 0.1895(3) 0.1816(2) 0.30181(12) 0.0303(7) Uani d . 1 . .
H H4 0.1999 0.1921 0.3439 0.036 Uiso calc R 1 . .
C C5 0.0968(3) 0.2395(2) 0.26867(11) 0.0269(6) Uani d . 1 . .
C C6 0.0771(3) 0.2229(2) 0.20780(12) 0.0264(6) Uani d . 1 . .
H H6 0.0129 0.2633 0.1857 0.032 Uiso calc R 1 . .
C C7 0.1528(3) 0.1459(2) 0.17905(12) 0.0255(6) Uani d . 1 . .
C C8 0.1169(3) 0.1222(2) 0.11452(12) 0.0267(6) Uani d . 1 . .
C C9 0.1212(3) 0.2048(2) 0.06972(11) 0.0246(6) Uani d . 1 . .
C C10 0.2006(3) 0.2915(2) 0.07938(11) 0.0256(6) Uani d . 1 . .
H H10 0.2518 0.2979 0.1158 0.031 Uiso calc R 1 . .
C C11 0.2069(3) 0.3687(2) 0.03726(11) 0.0250(6) Uani d . 1 . .
H H11 0.2634 0.4268 0.0442 0.030 Uiso calc R 1 . .
C C12 0.1289(3) 0.3597(2) -0.01543(12) 0.0267(6) Uani d . 1 . .
C C13 0.0496(3) 0.2727(2) -0.02606(12) 0.0308(7) Uani d . 1 . .
H H13 -0.0032 0.2668 -0.0621 0.037 Uiso calc R 1 . .
C C14 0.0480(3) 0.1956(2) 0.01559(12) 0.0294(6) Uani d . 1 . .
H H14 -0.0034 0.1356 0.0075 0.035 Uiso calc R 1 . .
C C15 0.2006(3) 0.5248(2) -0.04965(13) 0.0334(7) Uani d . 1 . .
H H15A 0.3020 0.5102 -0.0497 0.040 Uiso calc R 1 . .
H H15B 0.1756 0.5557 -0.0105 0.040 Uiso calc R 1 . .
C C16 0.1645(3) 0.5955(2) -0.10032(13) 0.0364(7) Uani d . 1 . .
H H16A 0.1906 0.5644 -0.1388 0.055 Uiso calc R 1 . .
H H16B 0.2154 0.6594 -0.0952 0.055 Uiso calc R 1 . .
H H16C 0.0638 0.6090 -0.1000 0.055 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O2 C15 . . 117.9(2) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 C7 . . 118.3(2) ?
C3 C2 C1 . . 119.5(2) ?
C7 C2 C1 . . 122.1(3) ?
C2 C3 C4 . . 122.0(3) ?
C2 C3 H3 . . 119.0 ?
C4 C3 H3 . . 119.0 ?
C5 C4 C3 . . 118.6(2) ?
C5 C4 H4 . . 120.7 ?
C3 C4 H4 . . 120.7 ?
C6 C5 C4 . . 121.4(3) ?
C6 C5 Br1 . . 119.3(2) ?
C4 C5 Br1 . . 119.3(2) ?
C5 C6 C7 . . 119.3(3) ?
C5 C6 H6 . . 120.4 ?
C7 C6 H6 . . 120.4 ?
C2 C7 C6 . . 120.4(3) ?
C2 C7 C8 . . 121.7(2) ?
C6 C7 C8 . . 117.8(2) ?
O1 C8 C9 . . 121.8(2) ?
O1 C8 C7 . . 119.4(2) ?
C9 C8 C7 . . 118.8(2) ?
C10 C9 C14 . . 118.6(3) ?
C10 C9 C8 . . 121.2(2) ?
C14 C9 C8 . . 120.2(2) ?
C11 C10 C9 . . 121.7(2) ?
C11 C10 H10 . . 119.2 ?
C9 C10 H10 . . 119.2 ?
C10 C11 C12 . . 118.8(3) ?
C10 C11 H11 . . 120.6 ?
C12 C11 H11 . . 120.6 ?
O2 C12 C11 . . 124.0(2) ?
O2 C12 C13 . . 115.7(2) ?
C11 C12 C13 . . 120.2(2) ?
C14 C13 C12 . . 120.0(3) ?
C14 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C13 C14 C9 . . 120.6(3) ?
C13 C14 H14 . . 119.7 ?
C9 C14 H14 . . 119.7 ?
O2 C15 C16 . . 107.2(2) ?
O2 C15 H15A . . 110.3 ?
C16 C15 H15A . . 110.3 ?
O2 C15 H15B . . 110.3 ?
C16 C15 H15B . . 110.3 ?
H15A C15 H15B . . 108.5 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C5 . 1.903(3) ?
O1 C8 . 1.230(3) ?
O2 C12 . 1.365(3) ?
O2 C15 . 1.442(3) ?
C1 C2 . 1.509(4) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C2 C3 . 1.389(4) ?
C2 C7 . 1.400(4) ?
C3 C4 . 1.388(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.382(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.382(4) ?
C6 C7 . 1.401(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.506(4) ?
C8 C9 . 1.475(4) ?
C9 C10 . 1.389(4) ?
C9 C14 . 1.397(4) ?
C10 C11 . 1.385(4) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.393(4) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.396(4) ?
C13 C14 . 1.374(4) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 C16 . 1.502(4) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C11 H11 O1 8_665 0.95 2.42 3.313(3) 155.8
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C2 C3 C4 . . . . -0.7(4) ?
C1 C2 C3 C4 . . . . 176.7(3) ?
C2 C3 C4 C5 . . . . -1.8(4) ?
C3 C4 C5 C6 . . . . 2.2(4) ?
C3 C4 C5 Br1 . . . . -177.0(2) ?
C4 C5 C6 C7 . . . . -0.1(4) ?
Br1 C5 C6 C7 . . . . 179.1(2) ?
C3 C2 C7 C6 . . . . 2.8(4) ?
C1 C2 C7 C6 . . . . -174.6(3) ?
C3 C2 C7 C8 . . . . -172.7(2) ?
C1 C2 C7 C8 . . . . 10.0(4) ?
C5 C6 C7 C2 . . . . -2.4(4) ?
C5 C6 C7 C8 . . . . 173.2(2) ?
C2 C7 C8 O1 . . . . 53.5(4) ?
C6 C7 C8 O1 . . . . -122.1(3) ?
C2 C7 C8 C9 . . . . -128.8(3) ?
C6 C7 C8 C9 . . . . 55.6(3) ?
O1 C8 C9 C10 . . . . -159.8(3) ?
C7 C8 C9 C10 . . . . 22.6(4) ?
O1 C8 C9 C14 . . . . 18.3(4) ?
C7 C8 C9 C14 . . . . -159.3(3) ?
C14 C9 C10 C11 . . . . 0.9(4) ?
C8 C9 C10 C11 . . . . 179.0(2) ?
C9 C10 C11 C12 . . . . 1.5(4) ?
C15 O2 C12 C11 . . . . -0.1(4) ?
C15 O2 C12 C13 . . . . 179.1(2) ?
C10 C11 C12 O2 . . . . 177.1(2) ?
C10 C11 C12 C13 . . . . -2.0(4) ?
O2 C12 C13 C14 . . . . -179.0(3) ?
C11 C12 C13 C14 . . . . 0.2(4) ?
C12 C13 C14 C9 . . . . 2.2(4) ?
C10 C9 C14 C13 . . . . -2.8(4) ?
C8 C9 C14 C13 . . . . 179.1(3) ?
C12 O2 C15 C16 . . . . -174.5(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745534
2 PubChem 46206447
