#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/84/2208474.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_2208474
loop_
_publ_author_name
'Frye, Brian C.'
'Mashuta, Mark S.'
'Mullins, Christopher S.'
'Grapperhaus, Craig A.'
'Buchanan, Robert M.'
_publ_section_title
;
 Ethyl 1-methylimidazole-2-carboxylate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1548
_journal_page_last               o1549
_journal_paper_doi               10.1107/S1600536806010038
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C7 H10 N2 O2'
_chemical_formula_moiety         'C7 H10 N2 O2'
_chemical_formula_sum            'C7 H10 N2 O2'
_chemical_formula_weight         154.17
_chemical_melting_point          .43E-42
_chemical_name_common            'Ethyl 1-methyimidazole-2-carboxylate '
_chemical_name_systematic
;
 ethyl 1-methyimidazole-2-carboxylate
;
_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                 112.797(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1040(8)
_cell_length_b                   15.2244(18)
_cell_length_c                   7.4511(9)
_cell_measurement_reflns_used    5362
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.96
_cell_measurement_theta_min      2.66
_cell_volume                     742.92(15)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS90 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean no
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'ω scans'
_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  0.0134
_diffrn_reflns_av_sigmaI/netI    0.0125
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6360
_diffrn_reflns_theta_full        27.96
_diffrn_reflns_theta_max         27.96
_diffrn_reflns_theta_min         3.11
_diffrn_standards_decay_%        <0.1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2001)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0301
_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/[σ²(Fo²)+(0.0213P)²+0.3603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0681
_reflns_number_gt                1636
_reflns_number_total             1728
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac2012.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               2208474
_cod_database_fobs_code          2208474
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O O1 0.25020(11) 0.57084(4) 0.39888(9) 0.01830(16) Uani d 1
O O2 0.23052(11) 0.46091(5) 0.59352(10) 0.02000(17) Uani d 1
N N1 0.24441(12) 0.45189(5) 0.11144(11) 0.01505(17) Uani d 1
N N2 0.19787(12) 0.34172(5) 0.28830(12) 0.01794(18) Uani d 1
C C1 0.22529(13) 0.42764(6) 0.28103(13) 0.01515(19) Uani d 1
C C2 0.20018(15) 0.30936(7) 0.11812(14) 0.0192(2) Uani d 1
H H2 0.1833(19) 0.2486(9) 0.0843(18) 0.022(3) Uiso d 1
C C3 0.22843(14) 0.37615(7) 0.00771(14) 0.0180(2) Uani d 1
H H3 0.2360(19) 0.3774(8) -0.1166(19) 0.022(3) Uiso d 1
C C4 0.27853(15) 0.53886(6) 0.04420(14) 0.0173(2) Uani d 1
H H4A 0.1699(19) 0.5784(8) 0.0380(17) 0.020(3) Uiso d 1
H H4B 0.4083(19) 0.5623(8) 0.1334(18) 0.019(3) Uiso d 1
H H4C 0.2773(19) 0.5313(8) -0.0873(19) 0.023(3) Uiso d 1
C C5 0.23488(13) 0.48678(6) 0.44178(13) 0.01523(19) Uani d 1
C C6 0.25898(15) 0.63570(6) 0.54630(14) 0.0177(2) Uani d 1
H H6A 0.3709(18) 0.6192(7) 0.6676(17) 0.015(3) Uiso d 1
H H6B 0.1307(18) 0.6334(8) 0.5636(17) 0.017(3) Uiso d 1
C C7 0.29400(17) 0.72322(7) 0.46991(15) 0.0217(2) Uani d 1
H H7A 0.304(2) 0.7695(10) 0.567(2) 0.036(4) Uiso d 1
H H7B 0.179(2) 0.7379(9) 0.347(2) 0.028(3) Uiso d 1
H H7C 0.421(2) 0.7219(8) 0.4487(19) 0.027(3) Uiso d 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0256(4) 0.0166(3) 0.0149(3) -0.0012(3) 0.0102(3) -0.0018(3)
O2 0.0254(4) 0.0216(4) 0.0146(3) -0.0001(3) 0.0095(3) 0.0010(3)
N1 0.0156(4) 0.0169(4) 0.0131(4) 0.0002(3) 0.0059(3) 0.0001(3)
N2 0.0186(4) 0.0174(4) 0.0181(4) -0.0004(3) 0.0074(3) 0.0000(3)
C1 0.0145(4) 0.0179(4) 0.0132(4) 0.0004(3) 0.0056(3) 0.0014(3)
C2 0.0193(4) 0.0182(5) 0.0200(5) -0.0008(4) 0.0077(4) -0.0032(4)
C3 0.0177(4) 0.0206(5) 0.0160(4) 0.0000(4) 0.0069(4) -0.0030(4)
C4 0.0200(5) 0.0175(5) 0.0157(4) -0.0002(4) 0.0084(4) 0.0020(3)
C5 0.0122(4) 0.0186(5) 0.0145(4) 0.0003(3) 0.0046(3) 0.0000(3)
C6 0.0214(5) 0.0179(5) 0.0152(4) 0.0003(4) 0.0089(4) -0.0027(4)
C7 0.0276(5) 0.0183(5) 0.0211(5) 0.0006(4) 0.0116(4) -0.0002(4)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C5 O1 C6 116.89(7) no
C3 N1 C1 106.09(8) no
C3 N1 C4 123.76(8) no
C1 N1 C4 130.15(8) no
C1 N2 C2 105.24(8) no
N2 C1 N1 111.79(8) no
N2 C1 C5 121.92(8) no
N1 C1 C5 126.29(8) no
N2 C2 C3 110.28(9) no
N2 C2 H2 123.3(8) no
C3 C2 H2 126.4(8) no
N1 C3 C2 106.59(8) no
N1 C3 H3 120.7(8) no
C2 C3 H3 132.7(8) no
N1 C4 H4A 110.1(7) no
N1 C4 H4B 109.7(7) no
H4A C4 H4B 109.4(10) no
N1 C4 H4C 107.2(7) no
H4A C4 H4C 109.1(10) no
H4B C4 H4C 111.4(10) no
O2 C5 O1 124.81(9) no
O2 C5 C1 123.32(9) no
O1 C5 C1 111.87(8) no
O1 C6 C7 106.20(8) no
O1 C6 H6A 107.7(7) no
C7 C6 H6A 112.5(7) no
O1 C6 H6B 107.9(7) no
C7 C6 H6B 112.5(7) no
H6A C6 H6B 109.7(10) no
C6 C7 H7A 109.2(8) no
C6 C7 H7B 110.7(8) no
H7A C7 H7B 108.2(11) no
C6 C7 H7C 109.9(8) no
H7A C7 H7C 109.0(11) no
H7B C7 H7C 109.7(11) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 1.3338(12) no
O1 C6 1.4604(11) no
O2 C5 1.2089(12) no
N1 C3 1.3682(12) no
N1 C1 1.3728(12) no
N1 C4 1.4686(12) no
N2 C1 1.3266(12) no
N2 C2 1.3664(13) no
C1 C5 1.4787(13) no
C2 C3 1.3707(14) no
C2 H2 0.954(13) no
C3 H3 0.948(13) no
C4 H4A 0.966(12) no
C4 H4B 0.972(12) no
C4 H4C 0.983(13) no
C6 C7 1.5070(14) no
C6 H6A 0.977(12) no
C6 H6B 0.969(12) no
C7 H7A 0.991(15) no
C7 H7B 0.988(14) no
C7 H7C 0.974(13) no
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_publ_flag
C2 N2 C1 N1 0.25(10) no
C2 N2 C1 C5 -179.19(8) no
C3 N1 C1 N2 -0.20(10) no
C4 N1 C1 N2 -179.26(9) no
C3 N1 C1 C5 179.20(8) no
C4 N1 C1 C5 0.14(15) no
C1 N2 C2 C3 -0.20(11) no
C1 N1 C3 C2 0.06(10) no
C4 N1 C3 C2 179.20(8) no
N2 C2 C3 N1 0.09(11) no
C6 O1 C5 O2 -1.01(13) no
C6 O1 C5 C1 179.45(7) no
N2 C1 C5 O2 4.43(14) no
N1 C1 C5 O2 -174.91(9) no
N2 C1 C5 O1 -176.02(8) no
N1 C1 C5 O1 4.63(13) no
C5 O1 C6 C7 175.23(8) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3469434
