#------------------------------------------------------------------------------
#$Date: 2016-02-13 21:28:24 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176429 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/11/2241147.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_2241147
loop_
_publ_author_name
'Stein, Timo'
'Hoffmann, Frank'
'Fröba, Michael'
_publ_section_title
;
 Crystal structures of
 1-bromo-3,5-bis(4,4-dimethyl-1,3-oxazolin-2-yl)benzene 0.15-hydrate and
 3,5-bis(4,4-dimethyl-1,3-oxazolin-2-yl)-1-iodobenzene
;
_journal_coeditor_code           LH5783
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1125
_journal_page_last               1131
_journal_paper_doi               10.1107/S2056989015016059
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C16 H19 Br N2 O2, 0.15H2 O'
_chemical_formula_moiety         'C16 H19 Br N2 O2, 0.15(H2 O)'
_chemical_formula_sum            'C16 H19.3 Br N2 O2.15'
_chemical_formula_weight         353.94
_chemical_name_systematic
;
1-Bromo-3,5-bis(4,4-dimethyl-1,3-oxazolin-2-yl)benzene
0.15-hydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 114.496(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.06610(10)
_cell_length_b                   16.2960(2)
_cell_length_c                   11.04000(10)
_cell_measurement_reflns_used    11733
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.7760
_cell_measurement_theta_min      3.2150
_cell_volume                     1647.97(4)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), OLEX2 (Dolomanov et al.,  2009),
publCIF (Westrip, 2010) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SUPERFLIP (Palatinus & Chapuis, 2007)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4127
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
'Agilent SuperNova Dual Source diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29541
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.496
_diffrn_reflns_theta_min         3.219
_exptl_absorpt_coefficient_mu    2.501
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPRO; Agilent, 2013)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             726
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.743
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         5438
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0351
_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)+(0.0278P)²+1.5569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0803
_reflns_number_gt                4598
_reflns_number_total             5438
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5783sup1.cif
_cod_data_source_block           1
_cod_original_cell_volume        1647.96(4)
_cod_original_formula_sum        'C16 H19.30 Br N2 O2.15'
_cod_database_code               2241147
_cod_database_fobs_code          2241147
#BEGIN Tags that were not found in dictionaries:
_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_min   0.483
_shelx_estimated_absorpt_t_max   0.825
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_occupancy
C C1 0.26376(17) 0.48374(9) 0.34172(15) 0.0162(3) Uani d 1
C C3 0.44468(17) 0.38604(9) 0.47611(15) 0.0161(3) Uani d 1
C C5 0.45798(18) 0.44445(10) 0.28229(15) 0.0180(3) Uani d 1
C C4 0.51639(17) 0.39301(10) 0.39218(15) 0.0176(3) Uani d 1
H H4 0.6035 0.3631 0.4099 0.021 Uiso calc 1
C C12 0.49957(17) 0.32940(10) 0.59022(16) 0.0184(3) Uani d 1
C C7 0.13236(18) 0.53354(9) 0.31540(15) 0.0172(3) Uani d 1
C C6 0.33230(18) 0.48959(10) 0.25469(15) 0.0179(3) Uani d 1
H H6 0.2934 0.5238 0.1783 0.022 Uiso calc 1
C C9 -0.0526(2) 0.62058(12) 0.23624(19) 0.0268(4) Uani d 1
C C14 0.53332(19) 0.25360(11) 0.76730(17) 0.0226(3) Uani d 1
C C16 0.4386(3) 0.18050(16) 0.7561(4) 0.0682(10) Uani d 1
H H16A 0.4962 0.1380 0.8186 0.102 Uiso calc 1
H H16B 0.4009 0.1589 0.6651 0.102 Uiso calc 1
H H16C 0.3568 0.1968 0.7771 0.102 Uiso calc 1
C C15 0.5965(4) 0.28651(17) 0.9079(2) 0.0632(9) Uani d 1
H H15A 0.6590 0.2447 0.9687 0.095 Uiso calc 1
H H15B 0.5170 0.3004 0.9336 0.095 Uiso calc 1
H H15C 0.6544 0.3357 0.9127 0.095 Uiso calc 1
C C2 0.31925(17) 0.43183(9) 0.45143(15) 0.0159(3) Uani d 1
H H2 0.2716 0.4276 0.5096 0.019 Uiso calc 1
C C13 0.6535(3) 0.2366(2) 0.7218(3) 0.0757(12) Uani d 1
H H13A 0.7495 0.2531 0.7914 0.091 Uiso calc 1
H H13B 0.6568 0.1775 0.7028 0.091 Uiso calc 1
C C8 -0.0606(2) 0.57193(12) 0.35229(19) 0.0257(4) Uani d 1
H H8A -0.0676 0.6094 0.4201 0.031 Uiso calc 1
H H8B -0.1460 0.5347 0.3203 0.031 Uiso calc 1
C C10 -0.0128(3) 0.70964(14) 0.2754(3) 0.0525(7) Uani d 1
H H10A -0.0925 0.7364 0.2894 0.079 Uiso calc 1
H H10B 0.0031 0.7380 0.2043 0.079 Uiso calc 1
H H10C 0.0766 0.7120 0.3578 0.079 Uiso calc 1
C C11 -0.1925(3) 0.6130(2) 0.1101(2) 0.0564(8) Uani d 1
H H11A -0.2755 0.6304 0.1283 0.085 Uiso calc 1
H H11C -0.2061 0.5558 0.0801 0.085 Uiso calc 1
H H11B -0.1859 0.6479 0.0405 0.085 Uiso calc 1
N N2 0.44454(16) 0.31821(9) 0.67357(14) 0.0217(3) Uani d 1
N N1 0.07115(17) 0.58157(10) 0.21786(15) 0.0248(3) Uani d 1
O O2 0.61878(15) 0.28455(9) 0.60266(13) 0.0309(3) Uani d 1
O O1 0.07500(14) 0.52563(8) 0.40654(13) 0.0257(3) Uani d 1
Br Br1 0.55330(2) 0.45321(2) 0.16706(2) 0.02642(6) Uani d 1
O O3 0.0751(12) 0.5663(7) -0.0328(10) 0.035(2) Uani d 0.15
H H3A 0.076(18) 0.572(11) 0.043(8) 0.050 Uiso d 0.15
H H3B 0.010(15) 0.532(9) -0.071(14) 0.050 Uiso d 0.15
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'
N N 0.0061 0.0033 '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
C2 C1 C6 120.34(15)
C2 C1 C7 120.67(14)
C6 C1 C7 118.99(14)
C2 C3 C4 120.20(14)
C2 C3 C12 119.44(14)
C4 C3 C12 120.35(14)
C6 C5 C4 122.04(15)
C6 C5 Br1 118.98(12)
C4 C5 Br1 118.98(13)
C5 C4 C3 118.75(15)
C5 C4 H4 120.6
C3 C4 H4 120.6
N2 C12 O2 118.75(15)
N2 C12 C3 126.08(15)
O2 C12 C3 115.16(14)
N1 C7 O1 118.85(15)
N1 C7 C1 126.06(15)
O1 C7 C1 115.09(13)
C5 C6 C1 118.59(14)
C5 C6 H6 120.7
C1 C6 H6 120.7
N1 C9 C10 108.11(16)
N1 C9 C11 110.53(19)
C10 C9 C11 111.9(2)
N1 C9 C8 103.30(14)
C10 C9 C8 110.73(19)
C11 C9 C8 111.89(17)
N2 C14 C16 109.10(15)
N2 C14 C15 109.82(16)
C16 C14 C15 110.5(2)
N2 C14 C13 103.34(15)
C16 C14 C13 113.3(3)
C15 C14 C13 110.6(2)
C14 C16 H16A 109.5
C14 C16 H16B 109.5
H16A C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C1 C2 C3 120.03(15)
C1 C2 H2 120.0
C3 C2 H2 120.0
O2 C13 C14 106.17(16)
O2 C13 H13A 110.5
C14 C13 H13A 110.5
O2 C13 H13B 110.5
C14 C13 H13B 110.5
H13A C13 H13B 108.7
O1 C8 C9 104.25(14)
O1 C8 H8A 110.9
C9 C8 H8A 110.9
O1 C8 H8B 110.9
C9 C8 H8B 110.9
H8A C8 H8B 108.9
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 C11 H11A 109.5
C9 C11 H11C 109.5
H11A C11 H11C 109.5
C9 C11 H11B 109.5
H11A C11 H11B 109.5
H11C C11 H11B 109.5
C12 N2 C14 106.82(14)
C7 N1 C9 106.76(15)
C12 O2 C13 104.63(15)
C7 O1 C8 105.11(13)
H3A O3 H3B 105(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.391(2)
C1 C6 1.399(2)
C1 C7 1.474(2)
C3 C2 1.393(2)
C3 C4 1.396(2)
C3 C12 1.472(2)
C5 C6 1.384(2)
C5 C4 1.389(2)
C5 Br1 1.8898(16)
C4 H4 0.9500
C12 N2 1.269(2)
C12 O2 1.362(2)
C7 N1 1.266(2)
C7 O1 1.358(2)
C6 H6 0.9500
C9 N1 1.485(2)
C9 C10 1.520(3)
C9 C11 1.520(3)
C9 C8 1.537(3)
C14 N2 1.487(2)
C14 C16 1.498(3)
C14 C15 1.511(3)
C14 C13 1.515(3)
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C2 H2 0.9500
C13 O2 1.443(3)
C13 H13A 0.9900
C13 H13B 0.9900
C8 O1 1.454(2)
C8 H8A 0.9900
C8 H8B 0.9900
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11C 0.9800
C11 H11B 0.9800
O3 H3A 0.84(2)
O3 H3B 0.84(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_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
C6 H6 O3 1_555 1_555 1_555 0.95 2.548(10) 3.395(10) 148.6(3) yes
O3 H3A N1 1_555 1_555 1_555 0.84(2) 1.96(2) 2.796(10) 178(15) yes
C16 H16B O3 1_555 1_555 2_545 0.98 2.181(10) 3.045(11) 146.2(3) yes
C13 H13B O3 1_555 1_555 2_545 0.99 2.940(10) 3.656(12) 130.4(3) yes
C8 H8B Br1 1_555 1_555 1_455 0.99 3.08869(19) 4.054(2) 165.38(10) yes
C11 H11C O3 1_555 1_555 3_565 0.98 2.557(11) 3.391(12) 142.9(3) yes
O3 H3B N1 1_555 1_555 3_565 0.84(2) 2.37(9) 3.107(11) 148(15) yes
O3 H3B O3 1_555 1_555 3_565 0.84(2) 2.32(13) 2.90(2) 126(13) yes
