#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/67/2206790.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_2206790
loop_
_publ_author_name
'Xiang Chao Zeng'
_publ_section_title
;
 Ethyl (4-bromo-1H-pyrrole-2-carboxamido)acetate
;
_journal_coeditor_code           SJ6125
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2958
_journal_page_last               o2960
_journal_paper_doi               10.1107/S1600536805024906
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C9 H11 Br N2 O3'
_chemical_formula_moiety         'C9 H11 Br N2 O3'
_chemical_formula_sum            'C9 H11 Br N2 O3'
_chemical_formula_weight         275.11
_chemical_melting_point          181
_chemical_name_systematic
;
Ethyl (4-bromo-1H-pyrrole-2-carboxamido)acetate
;
_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                 107.843(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.944(2)
_cell_length_b                   5.0501(8)
_cell_length_c                   16.264(3)
_cell_measurement_reflns_used    1926
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.58
_cell_volume                     1168.4(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6732
_diffrn_reflns_theta_full        27.02
_diffrn_reflns_theta_max         27.02
_diffrn_reflns_theta_min         2.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.508
_exptl_absorpt_correction_T_max  0.303
_exptl_absorpt_correction_T_min  0.202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       Block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.337
_refine_ls_extinction_coef       0.0053(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0463P)²+0.5034P] where P=  (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                1562
_reflns_number_total             2550
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj6125.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206790
_cod_database_fobs_code          2206790
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_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_type_symbol
Br1 0.09732(2) 0.27459(10) -0.00515(3) 0.1090(3) Uani d . 1 Br
C1 0.2661(2) 0.0278(6) -0.01976(18) 0.0576(7) Uani d . 1 C
H1 0.2343 -0.1065 -0.0562 0.069 Uiso calc R 1 H
C2 0.2264(2) 0.2253(6) 0.01464(19) 0.0595(8) Uani d . 1 C
C3 0.29750(18) 0.3852(6) 0.06599(17) 0.0533(7) Uani d . 1 C
H3 0.2901 0.5329 0.0975 0.064 Uiso calc R 1 H
C4 0.38099(19) 0.2819(5) 0.06104(16) 0.0432(6) Uani d . 1 C
C5 0.47844(18) 0.3672(5) 0.09482(15) 0.0429(6) Uani d . 1 C
C6 0.5911(2) 0.6769(5) 0.17947(18) 0.0507(6) Uani d . 1 C
H6A 0.5910 0.8386 0.2117 0.061 Uiso calc R 1 H
H6B 0.6116 0.7213 0.1300 0.061 Uiso calc R 1 H
C7 0.65965(18) 0.4850(5) 0.23595(17) 0.0471(6) Uani d . 1 C
C8 0.8196(3) 0.3596(12) 0.2849(3) 0.1242(18) Uani d . 1 C
H8A 0.8313 0.3953 0.3459 0.149 Uiso calc R 1 H
H8B 0.8004 0.1761 0.2740 0.149 Uiso calc R 1 H
C9 0.9024(4) 0.406(2) 0.2617(4) 0.220(4) Uani d . 1 C
H9A 0.8872 0.4080 0.2000 0.330 Uiso calc R 1 H
H9B 0.9471 0.2675 0.2850 0.330 Uiso calc R 1 H
H9C 0.9290 0.5734 0.2846 0.330 Uiso calc R 1 H
N1 0.36012(15) 0.0636(4) 0.00885(13) 0.0483(5) Uani d . 1 N
H1A 0.4007 -0.0358 -0.0038 0.058 Uiso calc R 1 H
N2 0.49743(14) 0.5732(4) 0.14961(13) 0.0479(5) Uani d . 1 N
H2 0.4536 0.6426 0.1667 0.057 Uiso calc R 1 H
O1 0.54214(13) 0.2578(3) 0.07369(12) 0.0532(5) Uani d . 1 O
O2 0.64098(14) 0.3132(4) 0.27816(13) 0.0599(5) Uani d . 1 O
O3 0.74556(14) 0.5333(5) 0.23359(15) 0.0795(7) Uani d . 1 O
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
Br1 0.0461(2) 0.1456(5) 0.1290(4) 0.0081(2) 0.0175(2) -0.0253(3)
C1 0.0562(17) 0.0594(18) 0.0543(16) -0.0034(14) 0.0127(13) -0.0054(14)
C2 0.0437(15) 0.071(2) 0.0627(17) 0.0068(14) 0.0154(14) -0.0036(15)
C3 0.0513(16) 0.0545(17) 0.0564(16) 0.0092(13) 0.0197(13) -0.0066(14)
C4 0.0519(14) 0.0391(14) 0.0412(13) 0.0058(11) 0.0181(11) 0.0002(11)
C5 0.0511(15) 0.0393(14) 0.0410(13) 0.0086(11) 0.0180(11) 0.0034(11)
C6 0.0591(17) 0.0396(14) 0.0571(16) -0.0015(12) 0.0235(14) 0.0010(12)
C7 0.0486(15) 0.0480(15) 0.0487(14) -0.0026(12) 0.0210(12) 0.0006(13)
C8 0.054(2) 0.186(5) 0.132(4) 0.025(3) 0.028(2) 0.077(4)
C9 0.084(4) 0.408(13) 0.175(6) 0.080(6) 0.049(4) 0.081(7)
N1 0.0530(13) 0.0458(13) 0.0489(12) 0.0075(10) 0.0196(10) -0.0044(10)
N2 0.0466(12) 0.0456(13) 0.0548(12) 0.0053(10) 0.0205(10) -0.0080(11)
O1 0.0516(11) 0.0530(11) 0.0604(11) 0.0087(8) 0.0254(9) -0.0088(9)
O2 0.0604(12) 0.0609(12) 0.0599(11) -0.0068(10) 0.0205(10) 0.0187(10)
O3 0.0510(12) 0.1006(17) 0.0935(16) 0.0035(11) 0.0320(11) 0.0356(14)
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
N1 C1 C2 107.4(2)
N1 C1 H1 126.3
C2 C1 H1 126.3
C1 C2 C3 108.8(3)
C1 C2 Br1 125.5(2)
C3 C2 Br1 125.7(2)
C4 C3 C2 106.5(2)
C4 C3 H3 126.7
C2 C3 H3 126.7
N1 C4 C3 107.6(2)
N1 C4 C5 119.0(2)
C3 C4 C5 133.3(2)
O1 C5 N2 120.4(2)
O1 C5 C4 122.0(2)
N2 C5 C4 117.6(2)
N2 C6 C7 112.6(2)
N2 C6 H6A 109.1
C7 C6 H6A 109.1
N2 C6 H6B 109.1
C7 C6 H6B 109.1
H6A C6 H6B 107.8
O2 C7 O3 123.6(3)
O2 C7 C6 125.9(2)
O3 C7 C6 110.5(2)
C9 C8 O3 108.6(4)
C9 C8 H8A 110.0
O3 C8 H8A 110.0
C9 C8 H8B 110.0
O3 C8 H8B 110.0
H8A C8 H8B 108.3
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C1 N1 C4 109.7(2)
C1 N1 H1A 125.1
C4 N1 H1A 125.1
C5 N2 C6 119.6(2)
C5 N2 H2 120.2
C6 N2 H2 120.2
C7 O3 C8 116.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.872(3)
C1 N1 1.350(3)
C1 C2 1.365(4)
C1 H1 0.9300
C2 C3 1.391(4)
C3 C4 1.377(4)
C3 H3 0.9300
C4 N1 1.368(3)
C4 C5 1.455(4)
C5 O1 1.237(3)
C5 N2 1.343(3)
C6 N2 1.433(3)
C6 C7 1.502(4)
C6 H6A 0.9700
C6 H6B 0.9700
C7 O2 1.191(3)
C7 O3 1.319(3)
C8 C9 1.420(6)
C8 O3 1.457(4)
C8 H8A 0.9700
C8 H8B 0.9700
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
N1 H1A 0.8600
N2 H2 0.8600
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
N1 H1A O1 3_655 0.86 1.97 2.788(3) 159
N2 H2 O2 2_655 0.86 2.08 2.935(3) 174
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
N1 C1 C2 C3 -0.4(3)
N1 C1 C2 Br1 179.0(2)
C1 C2 C3 C4 0.7(3)
Br1 C2 C3 C4 -178.7(2)
C2 C3 C4 N1 -0.8(3)
C2 C3 C4 C5 175.3(3)
N1 C4 C5 O1 4.4(4)
C3 C4 C5 O1 -171.3(3)
N1 C4 C5 N2 -176.4(2)
C3 C4 C5 N2 7.8(4)
N2 C6 C7 O2 -25.9(4)
N2 C6 C7 O3 154.7(2)
C2 C1 N1 C4 -0.1(3)
C3 C4 N1 C1 0.5(3)
C5 C4 N1 C1 -176.2(2)
O1 C5 N2 C6 3.9(4)
C4 C5 N2 C6 -175.3(2)
C7 C6 N2 C5 -66.7(3)
O2 C7 O3 C8 1.3(5)
C6 C7 O3 C8 -179.3(3)
C9 C8 O3 C7 168.7(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128912
