#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/19/2221938.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_2221938
loop_
_publ_author_name
'Tang, Lin-Lin'
'Ye, Jiao'
'Liu, Qi-Xing'
'Hu, Ai-Xi'
_publ_section_title
;
 2-Bromo-4,4-dimethyl-1-(2,4,5-trimethoxyphenyl)pentan-3-one
;
_journal_coeditor_code           BT2955
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1359
_journal_paper_doi               10.1107/S1600536809018601
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H23 Br O4'
_chemical_formula_moiety         'C16 H23 Br O4'
_chemical_formula_sum            'C16 H23 Br O4'
_chemical_formula_weight         359.25
_chemical_melting_point_gt       366
_chemical_melting_point_lt       369
_chemical_name_systematic
;
2-Bromo-4,4-dimethyl-1-(2,4,5-trimethoxyphenyl)pentan-3-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.7520(10)
_cell_angle_beta                 106.1960(10)
_cell_angle_gamma                100.3530(10)
_cell_formula_units_Z            2
_cell_length_a                   9.0173(5)
_cell_length_b                   9.2086(5)
_cell_length_c                   11.4217(6)
_cell_measurement_reflns_used    4833
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.01
_cell_measurement_theta_min      2.41
_cell_volume                     836.51(8)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       ω
_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  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6537
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.469
_exptl_absorpt_correction_T_max  0.5939
_exptl_absorpt_correction_T_min  0.3704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0252
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0411P)²+0.3147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0731
_reflns_number_gt                2940
_reflns_number_total             3237
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2955.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2221938
_cod_database_fobs_code          2221938
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 1.06994(2) 0.86479(2) 0.12181(2) 0.03353(9) Uani d . 1 . .
C C1 0.8126(2) 0.6005(2) 0.07781(19) 0.0234(4) Uani d . 1 . .
H H1A 0.7458 0.6459 0.0216 0.028 Uiso calc R 1 . .
H H1B 0.8596 0.5309 0.0243 0.028 Uiso calc R 1 . .
C C2 0.9469(2) 0.7329(2) 0.19069(19) 0.0216(4) Uani d . 1 . .
H H2 0.8996 0.7993 0.2477 0.026 Uiso calc R 1 . .
C C3 1.0691(2) 0.6722(2) 0.27311(19) 0.0224(4) Uani d . 1 . .
C C4 1.1235(3) 0.7470(3) 0.4214(2) 0.0310(5) Uani d . 1 . .
C C5 1.2550(3) 0.6801(4) 0.4841(3) 0.0517(7) Uani d . 1 . .
H H5A 1.2123 0.5653 0.4571 0.078 Uiso calc R 1 . .
H H5B 1.2899 0.7282 0.5794 0.078 Uiso calc R 1 . .
H H5C 1.3468 0.7039 0.4560 0.078 Uiso calc R 1 . .
C C6 1.1885(3) 0.9271(3) 0.4661(3) 0.0466(6) Uani d . 1 . .
H H6A 1.2815 0.9533 0.4399 0.070 Uiso calc R 1 . .
H H6B 1.2213 0.9734 0.5613 0.070 Uiso calc R 1 . .
H H6C 1.1042 0.9696 0.4256 0.070 Uiso calc R 1 . .
C C7 0.9764(3) 0.7038(3) 0.4612(2) 0.0399(5) Uani d . 1 . .
H H7A 0.8945 0.7514 0.4249 0.060 Uiso calc R 1 . .
H H7B 1.0095 0.7439 0.5566 0.060 Uiso calc R 1 . .
H H7C 0.9316 0.5886 0.4274 0.060 Uiso calc R 1 . .
C C8 0.7081(2) 0.5042(2) 0.12787(18) 0.0214(4) Uani d . 1 . .
C C9 0.7162(2) 0.3520(2) 0.12133(19) 0.0230(4) Uani d . 1 . .
H H9 0.7914 0.3107 0.0881 0.028 Uiso calc R 1 . .
C C10 0.6174(2) 0.2603(2) 0.16207(19) 0.0223(4) Uani d . 1 . .
C C11 0.5060(2) 0.3213(2) 0.21148(19) 0.0222(4) Uani d . 1 . .
C C12 0.4989(2) 0.4740(2) 0.22142(19) 0.0222(4) Uani d . 1 . .
H H12 0.4255 0.5165 0.2565 0.027 Uiso calc R 1 . .
C C13 0.5997(2) 0.5642(2) 0.17981(19) 0.0221(4) Uani d . 1 . .
C C14 0.7250(3) 0.0427(3) 0.1048(2) 0.0342(5) Uani d . 1 . .
H H14A 0.6990 0.0390 0.0145 0.051 Uiso calc R 1 . .
H H14B 0.7131 -0.0648 0.1058 0.051 Uiso calc R 1 . .
H H14C 0.8361 0.1074 0.1563 0.051 Uiso calc R 1 . .
C C15 0.3096(3) 0.2861(3) 0.3105(3) 0.0386(5) Uani d . 1 . .
H H15A 0.3760 0.3772 0.3897 0.058 Uiso calc R 1 . .
H H15B 0.2506 0.2054 0.3341 0.058 Uiso calc R 1 . .
H H15C 0.2330 0.3198 0.2520 0.058 Uiso calc R 1 . .
C C16 0.4788(2) 0.7768(2) 0.2246(2) 0.0292(4) Uani d . 1 . .
H H16A 0.3724 0.7047 0.1671 0.044 Uiso calc R 1 . .
H H16B 0.4866 0.8811 0.2172 0.044 Uiso calc R 1 . .
H H16C 0.4939 0.7862 0.3151 0.044 Uiso calc R 1 . .
O O1 1.11572(18) 0.56644(17) 0.21908(15) 0.0306(3) Uani d . 1 . .
O O2 0.61793(17) 0.11030(16) 0.15966(15) 0.0291(3) Uani d . 1 . .
O O3 0.41020(17) 0.22188(16) 0.24643(15) 0.0283(3) Uani d . 1 . .
O O4 0.60042(16) 0.71626(16) 0.18717(15) 0.0281(3) Uani d . 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
C8 C1 C2 . . 110.66(16) ?
C8 C1 H1A . . 109.5 ?
C2 C1 H1A . . 109.5 ?
C8 C1 H1B . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 108.1 ?
C1 C2 C3 . . 112.96(15) ?
C1 C2 Br1 . . 109.43(13) ?
C3 C2 Br1 . . 105.97(12) ?
C1 C2 H2 . . 109.5 ?
C3 C2 H2 . . 109.5 ?
Br1 C2 H2 . . 109.5 ?
O1 C3 C4 . . 122.68(18) ?
O1 C3 C2 . . 119.30(17) ?
C4 C3 C2 . . 118.00(16) ?
C3 C4 C5 . . 109.50(18) ?
C3 C4 C6 . . 110.49(19) ?
C5 C4 C6 . . 109.6(2) ?
C3 C4 C7 . . 107.65(17) ?
C5 C4 C7 . . 109.5(2) ?
C6 C4 C7 . . 110.09(19) ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C4 C6 H6A . . 109.5 ?
C4 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C4 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C4 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C13 C8 C9 . . 118.31(17) ?
C13 C8 C1 . . 120.84(17) ?
C9 C8 C1 . . 120.84(17) ?
C10 C9 C8 . . 121.62(18) ?
C10 C9 H9 . . 119.2 ?
C8 C9 H9 . . 119.2 ?
O2 C10 C9 . . 125.42(17) ?
O2 C10 C11 . . 115.27(17) ?
C9 C10 C11 . . 119.30(17) ?
O3 C11 C12 . . 124.48(17) ?
O3 C11 C10 . . 115.70(16) ?
C12 C11 C10 . . 119.82(17) ?
C11 C12 C13 . . 119.80(17) ?
C11 C12 H12 . . 120.1 ?
C13 C12 H12 . . 120.1 ?
O4 C13 C12 . . 123.22(17) ?
O4 C13 C8 . . 115.67(17) ?
C12 C13 C8 . . 121.11(17) ?
O2 C14 H14A . . 109.5 ?
O2 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O2 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O3 C15 H15A . . 109.5 ?
O3 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O3 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O4 C16 H16A . . 109.5 ?
O4 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O4 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C10 O2 C14 . . 116.49(15) ?
C11 O3 C15 . . 116.98(15) ?
C13 O4 C16 . . 118.02(15) ?
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 C2 . 1.9693(18) ?
C1 C8 . 1.514(3) ?
C1 C2 . 1.519(3) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C3 . 1.536(3) ?
C2 H2 . 1.0000 ?
C3 O1 . 1.205(2) ?
C3 C4 . 1.525(3) ?
C4 C5 . 1.530(3) ?
C4 C6 . 1.533(3) ?
C4 C7 . 1.542(3) ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 C13 . 1.393(3) ?
C8 C9 . 1.398(3) ?
C9 C10 . 1.382(3) ?
C9 H9 . 0.9500 ?
C10 O2 . 1.374(2) ?
C10 C11 . 1.407(3) ?
C11 O3 . 1.365(2) ?
C11 C12 . 1.392(3) ?
C12 C13 . 1.393(3) ?
C12 H12 . 0.9500 ?
C13 O4 . 1.377(2) ?
C14 O2 . 1.429(2) ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 O3 . 1.422(3) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 O4 . 1.428(2) ?
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
_geom_hbond_publ_flag
C2 H2 O4 . 1.0000 2.5000 3.089(2) 117.00 yes
C16 H16B O2 1_565 0.9800 2.5700 3.465(3) 151.00 yes
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
C8 C1 C2 C3 . . . . 66.5(2) ?
C8 C1 C2 Br1 . . . . -175.74(12) ?
C1 C2 C3 O1 . . . . 43.4(2) ?
Br1 C2 C3 O1 . . . . -76.38(19) ?
C1 C2 C3 C4 . . . . -135.17(18) ?
Br1 C2 C3 C4 . . . . 105.03(17) ?
O1 C3 C4 C5 . . . . 6.3(3) ?
C2 C3 C4 C5 . . . . -175.18(19) ?
O1 C3 C4 C6 . . . . 127.1(2) ?
C2 C3 C4 C6 . . . . -54.3(2) ?
O1 C3 C4 C7 . . . . -112.6(2) ?
C2 C3 C4 C7 . . . . 65.9(2) ?
C2 C1 C8 C13 . . . . 74.0(2) ?
C2 C1 C8 C9 . . . . -107.0(2) ?
C13 C8 C9 C10 . . . . 1.5(3) ?
C1 C8 C9 C10 . . . . -177.55(18) ?
C8 C9 C10 O2 . . . . -179.66(18) ?
C8 C9 C10 C11 . . . . -0.1(3) ?
O2 C10 C11 O3 . . . . -2.0(2) ?
C9 C10 C11 O3 . . . . 178.37(17) ?
O2 C10 C11 C12 . . . . 178.26(17) ?
C9 C10 C11 C12 . . . . -1.4(3) ?
O3 C11 C12 C13 . . . . -178.37(18) ?
C10 C11 C12 C13 . . . . 1.4(3) ?
C11 C12 C13 O4 . . . . -179.61(17) ?
C11 C12 C13 C8 . . . . 0.1(3) ?
C9 C8 C13 O4 . . . . 178.22(17) ?
C1 C8 C13 O4 . . . . -2.7(3) ?
C9 C8 C13 C12 . . . . -1.5(3) ?
C1 C8 C13 C12 . . . . 177.52(18) ?
C9 C10 O2 C14 . . . . -3.0(3) ?
C11 C10 O2 C14 . . . . 177.39(18) ?
C12 C11 O3 C15 . . . . -7.3(3) ?
C10 C11 O3 C15 . . . . 172.93(18) ?
C12 C13 O4 C16 . . . . -7.7(3) ?
C8 C13 O4 C16 . . . . 172.52(17) ?
