#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/57/2205735.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_2205735
loop_
_publ_author_name
'Xiang-Chao Zeng'
'Yu-Xia Li'
'Shi-Hai Xu'
'Po-Run Liu'
_publ_section_title
;
 N-Methyl-3-(4-bromo-1H-pyrrole-2-carbonyl)aminopropionitrile
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1291
_journal_page_last               o1293
_journal_paper_doi               10.1107/S160053680501038X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C9 H10 Br N3 O'
_chemical_formula_moiety         'C9 H10 Br N3 O'
_chemical_formula_sum            'C9 H10 Br N3 O'
_chemical_formula_weight         256.11
_chemical_melting_point          397.15
_chemical_name_systematic
;
 ?
;
_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                 110.015(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.759(2)
_cell_length_b                   10.488(3)
_cell_length_c                   12.080(3)
_cell_measurement_reflns_used    863
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.78
_cell_measurement_theta_min      2.64
_cell_volume                     1042.7(5)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6363
_diffrn_reflns_theta_full        27.07
_diffrn_reflns_theta_max         27.07
_diffrn_reflns_theta_min         2.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.913
_exptl_absorpt_correction_T_max  0.334
_exptl_absorpt_correction_T_min  0.122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick,1996)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.988
_refine_diff_density_min         -0.982
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0431
_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)+(0.059P)²+1.0123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1203
_reflns_number_gt                1741
_reflns_number_total             2262
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6165.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.

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed
to 'multi-scan' 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:

'_chemical_melting_point' value '124\%' was changed to '397.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '124\%' was changed to '397.15' - it
was converted from degrees Celsius(C) to
Kelvins(K).

'_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.

'_exptl_absorpt_correction_type' value 'Multi-Scan'
changed to 'multi-scan' 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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2205735
_cod_database_fobs_code          2205735
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 0.71645(5) 0.55496(4) 0.79596(4) 0.0697(2) Uani d . 1 Br
O1 0.0410(3) 0.3522(2) 0.4524(2) 0.0507(6) Uani d . 1 O
N1 0.2552(3) 0.5231(2) 0.5809(2) 0.0397(6) Uani d . 1 N
H1 0.1574 0.5508 0.5497 0.048 Uiso calc R 1 H
N2 0.2284(3) 0.2159(2) 0.4332(2) 0.0397(6) Uani d . 1 N
N3 -0.1695(5) 0.3025(4) 0.1471(4) 0.0790(11) Uani d . 1 N
C1 0.3103(4) 0.4089(3) 0.5543(3) 0.0347(6) Uani d . 1 C
C2 0.4729(4) 0.4005(3) 0.6212(3) 0.0405(7) Uani d . 1 C
H2 0.5430 0.3338 0.6214 0.049 Uiso calc R 1 H
C3 0.5116(4) 0.5116(3) 0.6885(3) 0.0421(7) Uani d . 1 C
C4 0.3754(4) 0.5860(3) 0.6628(3) 0.0441(7) Uani d . 1 C
H4 0.3676 0.6649 0.6956 0.053 Uiso calc R 1 H
C5 0.1863(4) 0.3241(3) 0.4755(3) 0.0360(6) Uani d . 1 C
C6 0.1021(4) 0.1235(3) 0.3755(3) 0.0471(8) Uani d . 1 C
H6A 0.0093 0.1385 0.4002 0.057 Uiso calc R 1 H
H6B 0.1427 0.0386 0.4012 0.057 Uiso calc R 1 H
C7 0.0464(5) 0.1290(4) 0.2415(3) 0.0546(9) Uani d . 1 C
H7A 0.1405 0.1429 0.2180 0.066 Uiso calc R 1 H
H7B 0.0000 0.0471 0.2101 0.066 Uiso calc R 1 H
C8 -0.0731(5) 0.2284(4) 0.1892(3) 0.0561(9) Uani d . 1 C
C9 0.3939(4) 0.1797(4) 0.4448(4) 0.0562(9) Uani d . 1 C
H9A 0.3926 0.0987 0.4075 0.084 Uiso calc R 1 H
H9B 0.4587 0.1737 0.5267 0.084 Uiso calc R 1 H
H9C 0.4394 0.2430 0.4077 0.084 Uiso calc R 1 H
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 0.0466(3) 0.0767(3) 0.0695(3) 0.00091(18) -0.00099(19) -0.0218(2)
O1 0.0349(12) 0.0485(13) 0.0664(16) 0.0035(10) 0.0145(10) -0.0166(11)
N1 0.0346(13) 0.0338(13) 0.0517(16) 0.0035(10) 0.0159(11) -0.0053(11)
N2 0.0400(13) 0.0339(13) 0.0464(15) 0.0037(11) 0.0163(11) -0.0043(11)
N3 0.084(3) 0.063(2) 0.078(3) 0.000(2) 0.012(2) 0.005(2)
C1 0.0377(15) 0.0321(14) 0.0376(16) 0.0031(12) 0.0171(12) 0.0013(12)
C2 0.0392(16) 0.0373(15) 0.0447(18) 0.0064(13) 0.0140(13) 0.0023(13)
C3 0.0366(16) 0.0448(17) 0.0432(17) -0.0018(13) 0.0116(13) -0.0046(14)
C4 0.0431(17) 0.0381(16) 0.0526(19) -0.0031(13) 0.0184(15) -0.0118(14)
C5 0.0396(16) 0.0321(14) 0.0370(15) 0.0034(12) 0.0138(12) 0.0012(12)
C6 0.056(2) 0.0317(16) 0.055(2) -0.0018(14) 0.0201(16) -0.0062(14)
C7 0.063(2) 0.047(2) 0.055(2) -0.0040(16) 0.0215(18) -0.0161(16)
C8 0.067(2) 0.049(2) 0.048(2) -0.0134(19) 0.0143(18) -0.0063(17)
C9 0.051(2) 0.053(2) 0.068(2) 0.0129(16) 0.0243(18) -0.0115(17)
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
C4 N1 C1 110.6(3)
C4 N1 H1 124.7
C1 N1 H1 124.7
C5 N2 C6 118.8(3)
C5 N2 C9 125.1(3)
C6 N2 C9 116.1(3)
N1 C1 C2 107.1(3)
N1 C1 C5 116.1(3)
C2 C1 C5 136.5(3)
C1 C2 C3 106.6(3)
C1 C2 H2 126.7
C3 C2 H2 126.7
C4 C3 C2 108.9(3)
C4 C3 Br1 124.9(3)
C2 C3 Br1 126.2(2)
N1 C4 C3 106.8(3)
N1 C4 H4 126.6
C3 C4 H4 126.6
O1 C5 N2 120.5(3)
O1 C5 C1 118.3(3)
N2 C5 C1 121.2(3)
N2 C6 C7 113.5(3)
N2 C6 H6A 108.9
C7 C6 H6A 108.9
N2 C6 H6B 108.9
C7 C6 H6B 108.9
H6A C6 H6B 107.7
C8 C7 C6 114.1(3)
C8 C7 H7A 108.7
C6 C7 H7A 108.7
C8 C7 H7B 108.7
C6 C7 H7B 108.7
H7A C7 H7B 107.6
N3 C8 C7 177.7(4)
N2 C9 H9A 109.5
N2 C9 H9B 109.5
H9A C9 H9B 109.5
N2 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.875(3)
O1 C5 1.242(4)
N1 C4 1.344(4)
N1 C1 1.370(4)
N1 H1 0.8600
N2 C5 1.346(4)
N2 C6 1.456(4)
N2 C9 1.459(4)
N3 C8 1.132(5)
C1 C2 1.379(4)
C1 C5 1.473(4)
C2 C3 1.394(5)
C2 H2 0.9300
C3 C4 1.369(5)
C4 H4 0.9300
C6 C7 1.523(5)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.460(6)
C7 H7A 0.9700
C7 H7B 0.9700
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
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 H1 O1 3_566 0.86 2.01 2.808(3) 155
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
C4 N1 C1 C2 -0.9(4)
C4 N1 C1 C5 173.5(3)
N1 C1 C2 C3 0.6(3)
C5 C1 C2 C3 -172.0(3)
C1 C2 C3 C4 -0.2(4)
C1 C2 C3 Br1 -179.5(2)
C1 N1 C4 C3 0.8(4)
C2 C3 C4 N1 -0.4(4)
Br1 C3 C4 N1 179.0(2)
C6 N2 C5 O1 -9.3(4)
C9 N2 C5 O1 173.5(3)
C6 N2 C5 C1 167.9(3)
C9 N2 C5 C1 -9.2(5)
N1 C1 C5 O1 -10.0(4)
C2 C1 C5 O1 162.1(4)
N1 C1 C5 N2 172.7(3)
C2 C1 C5 N2 -15.2(5)
C5 N2 C6 C7 100.8(3)
C9 N2 C6 C7 -81.8(4)
N2 C6 C7 C8 -82.0(4)
C6 C7 C8 N3 -112(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21129585
