#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:27:18 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179664 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/17/4511722.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_4511722
loop_
_publ_author_name
'Yufit, D. S.'
'Shishkin, O. V.'
'Zubatyuk, R. I.'
'Howard, J. A. K.'
_publ_section_title
;
 Trimethyltrioxane (Paraldehyde) and Its Halomethanes Complexes:
 Crystallization, Structures, and Analysis of Packing Motifs
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4303
_journal_paper_doi               10.1021/cg500354t
_journal_volume                  14
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C H2 Br2, C6 H12 O3'
_chemical_formula_sum            'C7 H14 Br2 O3'
_chemical_formula_weight         306.00
_chemical_name_common
;
molecular complex (1:1) of paraldehyde with dibromomethane
;
_chemical_name_systematic
;
 2,4,6-trimethyl-1,3,5-trioxane dibromomethane (1:1)  
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_Hall           'P 2ac -2'
_space_group_name_H-M_alt        'P m n 21'
_symmetry_space_group_name_Hall  'P 2ac -2'
_symmetry_space_group_name_H-M   'P m n 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-02-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.01.22 svn.r2872 for OlexSys, GUI svn.r4754)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.016(2)
_cell_length_b                   10.6738(14)
_cell_length_c                   4.4634(5)
_cell_measurement_reflns_used    695
_cell_measurement_temperature    230.0(2)
_cell_measurement_theta_max      27.096
_cell_measurement_theta_min      2.551
_cell_volume                     572.46(14)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_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      230.0(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.778
_diffrn_measured_fraction_theta_max 0.778
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            4664
_diffrn_reflns_theta_full        29.49
_diffrn_reflns_theta_max         29.49
_diffrn_reflns_theta_min         1.91
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    7.053
_exptl_absorpt_correction_T_max  0.2326
_exptl_absorpt_correction_T_min  0.0013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2006/1 (Bruker,2006) was used for absorption correction.
R(int) was 0.1058 before and 0.0392 after correction.
The Ratio of minimum to maximum transmission is 0.0056.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(17)
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     68
_refine_ls_number_reflns         1234
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1223
_reflns_number_gt                963
_reflns_number_total             1234
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg500354t_si_001.cif
_cod_data_source_block           ndbmtmt
_cod_depositor_comments
'Adding full bibliography for 4511720--4511724.cif.'
_cod_original_cell_volume        572.45(14)
_cod_database_code               4511722
#BEGIN Tags that were not found in dictionaries:
_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 H(H,H) groups, All C(H,H,H) groups
2.a Everything fixed:
 H3A, H3B
2.b Ternary CH refined with riding coordinates:
 C2(H2)
2.c Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y, z'
4 'x+1/2, -y, 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_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Br1 Br 0.63235(3) 0.98123(5) 0.9612(6) 0.0628(3) Uani 1 d . . 1 . . .
C1S C 0.5000 0.9339(9) 0.750(2) 0.071(3) Uani 1 d . . 2 S T P
H1SA H 0.5000 0.9735 0.5540 0.085 Uiso 1 calc . . 2 RS T P
H1SB H 0.5000 0.8439 0.7198 0.085 Uiso 1 calc . . 2 RS T P
O1 O 0.5000 0.6596(4) 0.448(2) 0.0474(11) Uani 1 d . . 2 S T P
O2 O 0.5954(3) 0.4724(3) 0.460(3) 0.0532(9) Uani 1 d . . 1 . . .
C1 C 0.5967(5) 0.5966(6) 0.3505(14) 0.050(2) Uani 1 d A 2 1 . . .
C2 C 0.5000 0.4091(7) 0.359(2) 0.069(4) Uani 1 d . 1 2 S T P
H2 H 0.5000 0.4055 0.1399 0.082 Uiso 1 calc . 1 2 RS T P
C3 C 0.5000 0.2775(6) 0.486(4) 0.074(2) Uani 1 d . . 2 S T P
C4 C 0.6979(3) 0.6628(4) 0.469(2) 0.0636(13) Uani 1 d . . 1 . . .
H4A H 0.6942 0.6667 0.6832 0.095 Uiso 1 calc A . 1 GR . .
H4B H 0.7006 0.7462 0.3884 0.095 Uiso 1 calc A . 1 GR . .
H4C H 0.7635 0.6178 0.4095 0.095 Uiso 1 calc A . 1 GR . .
H1 H 0.595(4) 0.596(5) 0.146(13) 0.036(17) Uiso 1 d . . 1 . . .
H3A H 0.5655 0.2328 0.4224 0.054 Uiso 1 d . . 1 . . .
H3B H 0.5000 0.2804 0.7030 0.054 Uiso 1 d . . 2 S T P
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0380(3) 0.0801(4) 0.0703(7) -0.0078(10) 0.0019(7) -0.00638(17)
C1S 0.048(5) 0.096(7) 0.069(8) -0.020(6) 0.000 0.000
O1 0.046(2) 0.0374(19) 0.059(4) 0.004(5) 0.000 0.000
O2 0.0611(18) 0.0409(15) 0.057(3) -0.002(4) 0.003(7) 0.0060(12)
C1 0.058(3) 0.055(3) 0.035(8) 0.009(2) 0.011(2) 0.008(3)
C2 0.083(6) 0.047(4) 0.077(11) -0.014(4) 0.000 0.000
C3 0.104(5) 0.037(3) 0.080(7) -0.002(6) 0.000 0.000
C4 0.046(2) 0.058(3) 0.087(4) 0.003(7) -0.003(6) 0.0011(18)
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'
Br Br -0.2901 2.4595 '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'
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
Br1 C1S Br1 112.1(5) 3_655 .
Br1 C1S H1SA 109.2 3_655 .
Br1 C1S H1SA 109.2 . .
Br1 C1S H1SB 109.2 3_655 .
Br1 C1S H1SB 109.2 . .
H1SA C1S H1SB 107.9 . .
C1 O1 C1 110.9(6) 3_655 .
C2 O2 C1 110.6(8) . .
O1 C1 O2 109.3(5) . .
O1 C1 C4 109.5(5) . .
O1 C1 H1 107(3) . .
O2 C1 C4 109.3(6) . .
O2 C1 H1 109(3) . .
C4 C1 H1 112(3) . .
O2 C2 O2 109.5(8) . 3_655
O2 C2 H2 109.7 . .
O2 C2 H2 109.7 3_655 .
O2 C2 C3 109.1(6) 3_655 .
O2 C2 C3 109.1(6) . .
C3 C2 H2 109.7 . .
C2 C3 H3A 110.4 . .
C2 C3 H3B 110.2 . .
H3A C3 H3B 108.2 . .
C1 C4 H4A 109.5 . .
C1 C4 H4B 109.5 . .
C1 C4 H4C 109.5 . .
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1S 1.917(6) .
C1S Br1 1.917(6) 3_655
C1S H1SA 0.9700 .
C1S H1SB 0.9700 .
O1 C1 1.412(6) 3_655
O1 C1 1.412(6) .
O2 C1 1.413(9) .
O2 C2 1.403(7) .
C1 C4 1.501(8) .
C1 H1 0.91(5) .
C2 O2 1.403(7) 3_655
C2 H2 0.9800 .
C2 C3 1.515(12) .
C3 H3A 0.9642 .
C3 H3B 0.9672 .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
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
C1S H1SB O1 0.97 2.31 3.223(10) 156.3
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_4
C1 O1 C1 O2 -58.0(10) 3_655 .
C1 O2 C2 O2 -59.4(17) . 3_655
C2 O2 C1 O1 58.5(12) . .
C3 C2 O2 C1 -178.6(10) . .
C4 C1 O1 C1 -177.7(4) . 3_655
C4 C1 O2 C2 178.4(8) . .
