Synthesis of mesomeric betaine compounds with imidazolium-enolate structure.
Gonsior, Nina; Mohr, Fabian; Ritter, Helmut; Beilstein journal of organic chemistry 8 (2012) 390–397; doi:10.3762/bjoc.8.42

data_4029712
_publ_section_title
;
 Synthesis of mesomeric betaine compounds with imidazolium-enolate
 structure.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              390
_journal_page_last               397
_journal_paper_doi               10.3762/bjoc.8.42
_journal_volume                  8
_journal_year                    2012
_chemical_formula_moiety         'C13 H12 Br2 N2 O3'
_chemical_formula_sum            'C13 H12 Br2 N2 O3'
_chemical_formula_weight         404.07
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 93.428(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0119(6)
_cell_length_b                   3.99067(18)
_cell_length_c                   22.8802(9)
_cell_measurement_reflns_used    3157
_cell_measurement_temperature    150
_cell_measurement_theta_max      62.3394
_cell_measurement_theta_min      3.4266
_cell_volume                     1368.24(10)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
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_computing_molecular_graphics
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OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 16.2705
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
1 omega -106.00  -60.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-      -32.9646  179.0000 -150.0000 46

2 omega    6.00   95.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       32.9646   77.0000  150.0000 89

3 omega  -37.00   60.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       32.9646  -77.0000   30.0000 97

4 omega   67.00  162.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000   45.0000  -60.0000 95

5 omega   28.00   75.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  -45.0000 -180.0000 47

6 omega   45.00   72.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  -45.0000 -120.0000 27

7 omega   84.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  -77.0000  150.0000 31

8 omega  117.00  162.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000   45.0000 -120.0000 45

9 omega  127.00  153.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  111.0000 -180.0000 26

10 omega   24.00   82.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  -69.0000   67.0000 58

11 omega  125.00  158.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000   45.0000 -150.0000 33

12 omega  132.00  158.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000   77.0000  120.0000 26

13 omega   37.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  -45.0000  120.0000 40

14 omega   98.00  163.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  111.0000  -90.0000 65

15 omega   84.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000   45.0000 -150.0000 29

16 omega   93.00  134.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  111.0000 -120.0000 41

17 omega   54.00   81.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  -77.0000  150.0000 27

18 omega   34.00   60.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  179.0000  120.0000 26

19 omega   36.00   63.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  -45.0000   60.0000 27
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0820922
_diffrn_orient_matrix_UB_12      0.2087486
_diffrn_orient_matrix_UB_13      0.0209734
_diffrn_orient_matrix_UB_21      0.05913
_diffrn_orient_matrix_UB_22      -0.2157706
_diffrn_orient_matrix_UB_23      -0.0379398
_diffrn_orient_matrix_UB_31      -0.018185
_diffrn_orient_matrix_UB_32      0.2428524
_diffrn_orient_matrix_UB_33      -0.0516682
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4645
_diffrn_reflns_theta_full        62.43
_diffrn_reflns_theta_max         62.43
_diffrn_reflns_theta_min         3.87
_exptl_absorpt_coefficient_mu    7.611
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.63508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'dark orange'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.962
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.878
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[\s^2^(Fo^2^)+(0.0698P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3
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_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0921
_reflns_number_gt                1899
_reflns_number_total             2161
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-8-42-S2.cif
_cod_data_source_block           DU_V44BU_CU
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/Beilstein/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_database_code               4029712