#------------------------------------------------------------------------------
#$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $
#$Revision: 88064 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/86/2018696.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_2018696
loop_
_publ_author_name
'Sonar, Vijayakumar N.'
'Parkin, Sean'
'Crooks, Peter A.'
_publ_section_title
;
The effect of hydrogen bonding on the conformations of
2-(1H-indol-3-yl)-2-oxoacetamide and
2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide
;
_journal_coeditor_code YP3017
_journal_issue 10
_journal_name_full 'Acta Crystallographica Section C'
_journal_page_first o405
_journal_page_last o407
_journal_volume 68
_journal_year 2012
_chemical_formula_iupac 'C10 H8 N2 O2'
_chemical_formula_moiety 'C10 H8 N2 O2'
_chemical_formula_sum 'C10 H8 N2 O2'
_chemical_formula_weight 188.18
_chemical_name_systematic
;
2-(1H-indol-3-yl)-2-oxoacetamide
;
_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 SHELXL97
_cell_angle_alpha 90.00
_cell_angle_beta 93.251(3)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 5.1253(4)
_cell_length_b 19.4363(14)
_cell_length_c 8.4953(6)
_cell_measurement_reflns_used 8721
_cell_measurement_temperature 90.0(2)
_cell_measurement_theta_max 68.95
_cell_measurement_theta_min 4.55
_cell_volume 844.91(11)
_computing_cell_refinement 'APEX2 (Bruker, 2006)'
_computing_data_collection 'APEX2 (Bruker, 2006)'
_computing_data_reduction 'APEX2 (Bruker, 2006)'
_computing_molecular_graphics 'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and local procedures
;
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type 'Bruker X8 Proteum'
_diffrn_measurement_method '\f and \w'
_diffrn_radiation_monochromator 'graded multilayer optics'
_diffrn_radiation_source 'fine-focus rotating anode'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_reflns_av_R_equivalents 0.0424
_diffrn_reflns_av_sigmaI/netI 0.0286
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_h_min -4
_diffrn_reflns_limit_k_max 23
_diffrn_reflns_limit_k_min -23
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_number 10887
_diffrn_reflns_theta_full 68.94
_diffrn_reflns_theta_max 68.94
_diffrn_reflns_theta_min 4.55
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.880
_exptl_absorpt_correction_T_max 0.949
_exptl_absorpt_correction_T_min 0.744
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
[SADABS (Bruker, 2006) and XABS2 (Parkin et al., 1995)]
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.479
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 392
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.06
_refine_diff_density_max 0.325
_refine_diff_density_min -0.330
_refine_ls_extinction_coef 0.0033(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref 1.235
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 128
_refine_ls_number_reflns 1518
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.235
_refine_ls_R_factor_all 0.0585
_refine_ls_R_factor_gt 0.0575
_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/[\s^2^(Fo^2^)+(0.0370P)^2^+1.8838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1576
_refine_ls_wR_factor_ref 0.1581
_reflns_number_gt 1481
_reflns_number_total 1518
_reflns_threshold_expression I>2\s(I)
_iucr_refine_instructions_details
;
TITL I in P2(1)/c
CELL 1.54178 5.1253 19.4363 8.4953 90.000 93.251 90.000
ZERR 4.00 0.0004 0.0014 0.0006 0.000 0.003 0.000
LATT 1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C H N O
UNIT 40 32 8 8
TEMP -183
SIZE 0.30 0.08 0.06
L.S. 4
BOND
BOND $H
CONF
HTAB
EQIV $1 x-1, -y+3/2, z+1/2
EQIV $2 -x+1, -y+1, -z+1
EQIV $3 x+1, y, z
HTAB N1 O1_$1
HTAB N2 O2_$2
HTAB N2 O2_$3
ACTA
FMAP 2
PLAN 10
WGHT 0.037000 1.883800
EXTI 0.003301
FVAR 0.67359
N1 3 0.078234 0.771518 0.555815 11.00000 0.01454 0.03251 =
0.02130 -0.00254 0.00359 0.00380
AFIX 43
H1 2 -0.052943 0.776595 0.617299 11.00000 -1.20000
AFIX 0
N2 3 0.727230 0.560111 0.410322 11.00000 0.00938 0.02114 =
0.03564 0.00276 0.00437 -0.00075
AFIX 93
H2A 2 0.724226 0.516294 0.436239 11.00000 -1.20000
H2B 2 0.876127 0.579961 0.390435 11.00000 -1.20000
AFIX 0
O1 4 0.725312 0.683647 0.268382 11.00000 0.01379 0.02855 =
0.02473 0.00191 0.00718 -0.00030
O2 4 0.291594 0.572395 0.427152 11.00000 0.01200 0.02395 =
0.03353 0.00309 0.00372 -0.00024
C1 1 0.182612 0.711677 0.518140 11.00000 0.01419 0.02691 =
0.01749 0.00013 0.00065 0.00093
AFIX 43
H1A 2 0.128208 0.668057 0.554641 11.00000 -1.20000
AFIX 0
C2 1 0.205396 0.824523 0.484538 11.00000 0.01552 0.02759 =
0.01858 -0.00355 -0.00279 0.00181
C3 1 0.159205 0.894619 0.491757 11.00000 0.02210 0.02946 =
0.03009 -0.00791 -0.00368 0.00433
AFIX 43
H3 2 0.025381 0.912917 0.552409 11.00000 -1.20000
AFIX 0
C4 1 0.316373 0.936660 0.406862 11.00000 0.02740 0.02315 =
0.03748 -0.00300 -0.00713 0.00394
AFIX 43
H4 2 0.288013 0.984962 0.406770 11.00000 -1.20000
AFIX 0
C5 1 0.516341 0.909381 0.321121 11.00000 0.02392 0.02607 =
0.03019 0.00229 -0.00493 -0.00391
AFIX 43
H5 2 0.624939 0.939649 0.266265 11.00000 -1.20000
AFIX 0
C6 1 0.559724 0.839631 0.314261 11.00000 0.01672 0.02684 =
0.02373 0.00049 -0.00161 -0.00119
AFIX 43
H6 2 0.695829 0.821751 0.254803 11.00000 -1.20000
AFIX 0
C7 1 0.400616 0.795622 0.396023 11.00000 0.01295 0.02531 =
0.01710 -0.00012 -0.00244 0.00093
C8 1 0.383408 0.722229 0.417334 11.00000 0.01239 0.02292 =
0.01946 -0.00028 0.00107 0.00146
C9 1 0.546152 0.671197 0.354181 11.00000 0.01179 0.02378 =
0.02001 0.00065 0.00087 -0.00112
C10 1 0.507817 0.596156 0.401251 11.00000 0.01283 0.02449 =
0.02062 -0.00102 0.00276 -0.00030
HKLF 4
REM x07115 in P2(1)/c
REM R1 = 0.0575 for 1481 Fo > 4sig(Fo) and 0.0585 for all 1518 data
REM 128 parameters refined using 0 restraints
END
WGHT 0.0370 1.8828
REM Highest difference peak 0.325, deepest hole -0.330, 1-sigma level 0.080
Q1 1 0.4117 0.7574 0.4033 11.00000 0.05 0.32
Q2 1 0.2707 0.7136 0.4532 11.00000 0.05 0.30
Q3 1 0.5485 0.7518 0.1612 11.00000 0.05 0.28
Q4 1 0.2678 0.5197 0.4340 11.00000 0.05 0.27
Q5 1 0.1332 0.8046 0.5064 11.00000 0.05 0.25
Q6 1 0.5973 0.7987 0.1770 11.00000 0.05 0.25
Q7 1 0.1122 0.6133 0.5046 11.00000 0.05 0.24
Q8 1 0.4424 0.7015 0.3995 11.00000 0.05 0.24
Q9 1 0.3267 0.8091 0.4724 11.00000 0.05 0.24
Q10 1 0.2023 0.8545 0.4978 11.00000 0.05 0.23
;
_[local]_cod_data_source_file yp3017.cif
_[local]_cod_data_source_block I
_[local]_cod_cif_authors_sg_H-M 'P 21/c'
_cod_database_code 2018696
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 0.0782(5) 0.77152(13) 0.5558(3) 0.0227(6) Uani d . 1 1
H H1 -0.0529 0.7766 0.6173 0.027 Uiso calc R 1 1
N N2 0.7272(5) 0.56011(12) 0.4103(3) 0.0219(6) Uani d . 1 1
H H2A 0.7242 0.5163 0.4362 0.026 Uiso calc R 1 1
H H2B 0.8761 0.5800 0.3904 0.026 Uiso calc R 1 1
O O1 0.7253(4) 0.68365(10) 0.2684(2) 0.0221(5) Uani d . 1 1
O O2 0.2916(4) 0.57240(10) 0.4272(3) 0.0231(5) Uani d . 1 1
C C1 0.1826(5) 0.71168(15) 0.5181(3) 0.0195(6) Uani d . 1 1
H H1A 0.1282 0.6681 0.5546 0.023 Uiso calc R 1 1
C C2 0.2054(6) 0.82452(15) 0.4845(3) 0.0207(7) Uani d . 1 1
C C3 0.1592(6) 0.89462(16) 0.4918(4) 0.0274(7) Uani d . 1 1
H H3 0.0254 0.9129 0.5524 0.033 Uiso calc R 1 1
C C4 0.3164(6) 0.93666(16) 0.4069(4) 0.0297(8) Uani d . 1 1
H H4 0.2880 0.9850 0.4068 0.036 Uiso calc R 1 1
C C5 0.5163(6) 0.90938(16) 0.3211(4) 0.0270(7) Uani d . 1 1
H H5 0.6249 0.9396 0.2663 0.032 Uiso calc R 1 1
C C6 0.5597(6) 0.83963(15) 0.3143(4) 0.0225(7) Uani d . 1 1
H H6 0.6958 0.8218 0.2548 0.027 Uiso calc R 1 1
C C7 0.4006(5) 0.79562(15) 0.3960(3) 0.0186(6) Uani d . 1 1
C C8 0.3834(5) 0.72223(15) 0.4173(3) 0.0183(6) Uani d . 1 1
C C9 0.5462(5) 0.67120(15) 0.3542(3) 0.0185(6) Uani d . 1 1
C C10 0.5078(5) 0.59616(15) 0.4013(3) 0.0192(6) Uani d . 1 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
N1 0.0145(12) 0.0325(14) 0.0213(13) 0.0038(10) 0.0036(10) -0.0025(10)
N2 0.0094(11) 0.0211(13) 0.0356(15) -0.0008(9) 0.0044(10) 0.0028(10)
O1 0.0138(10) 0.0286(11) 0.0247(11) -0.0003(8) 0.0072(8) 0.0019(8)
O2 0.0120(10) 0.0239(11) 0.0335(12) -0.0002(8) 0.0037(8) 0.0031(9)
C1 0.0142(14) 0.0269(15) 0.0175(14) 0.0009(11) 0.0007(11) 0.0001(11)
C2 0.0155(14) 0.0276(16) 0.0186(15) 0.0018(11) -0.0028(11) -0.0035(11)
C3 0.0221(16) 0.0295(17) 0.0301(18) 0.0043(13) -0.0037(13) -0.0079(13)
C4 0.0274(17) 0.0231(16) 0.0375(19) 0.0039(13) -0.0071(14) -0.0030(13)
C5 0.0239(16) 0.0261(16) 0.0302(18) -0.0039(12) -0.0049(13) 0.0023(13)
C6 0.0167(15) 0.0268(16) 0.0237(16) -0.0012(12) -0.0016(12) 0.0005(12)
C7 0.0130(13) 0.0253(15) 0.0171(14) 0.0009(11) -0.0024(11) -0.0001(11)
C8 0.0124(13) 0.0229(14) 0.0195(14) 0.0015(11) 0.0011(11) -0.0003(11)
C9 0.0118(13) 0.0238(15) 0.0200(15) -0.0011(11) 0.0009(11) 0.0007(11)
C10 0.0128(14) 0.0245(15) 0.0206(15) -0.0003(11) 0.0028(11) -0.0010(11)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 N1 C2 110.0(2) ?
C1 N1 H1 125.0 ?
C2 N1 H1 125.0 ?
C10 N2 H2A 120.0 ?
C10 N2 H2B 120.0 ?
H2A N2 H2B 120.0 ?
N1 C1 C8 110.0(3) ?
N1 C1 H1A 125.0 ?
C8 C1 H1A 125.0 ?
N1 C2 C3 129.1(3) ?
N1 C2 C7 107.8(3) ?
C3 C2 C7 123.1(3) ?
C4 C3 C2 117.0(3) ?
C4 C3 H3 121.5 ?
C2 C3 H3 121.5 ?
C3 C4 C5 121.1(3) ?
C3 C4 H4 119.5 ?
C5 C4 H4 119.5 ?
C6 C5 C4 121.5(3) ?
C6 C5 H5 119.3 ?
C4 C5 H5 119.3 ?
C5 C6 C7 118.9(3) ?
C5 C6 H6 120.6 ?
C7 C6 H6 120.6 ?
C6 C7 C2 118.5(3) ?
C6 C7 C8 135.4(3) ?
C2 C7 C8 106.2(2) ?
C1 C8 C9 126.9(3) y
C1 C8 C7 106.0(2) ?
C9 C8 C7 127.0(3) ?
O1 C9 C8 124.1(3) y
O1 C9 C10 117.1(3) y
C8 C9 C10 118.7(2) ?
O2 C10 N2 124.1(3) y
O2 C10 C9 122.3(2) y
N2 C10 C9 113.5(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 1.327(4) ?
N1 C2 1.378(4) ?
N1 H1 0.8800 ?
N2 C10 1.323(4) y
N2 H2A 0.8800 ?
N2 H2B 0.8800 ?
O1 C9 1.228(3) ?
O2 C10 1.232(3) y
C1 C8 1.391(4) ?
C1 H1A 0.9500 ?
C2 C3 1.385(4) ?
C2 C7 1.403(4) ?
C3 C4 1.379(5) ?
C3 H3 0.9500 ?
C4 C5 1.395(5) ?
C4 H4 0.9500 ?
C5 C6 1.376(4) ?
C5 H5 0.9500 ?
C6 C7 1.394(4) ?
C6 H6 0.9500 ?
C7 C8 1.441(4) ?
C8 C9 1.421(4) y
C9 C10 1.528(4) y
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 4_476 0.88 1.92 2.768(3) 160.2
N2 H2A O2 3_666 0.88 2.08 2.926(3) 160.5
N2 H2B O2 1_655 0.88 2.14 2.898(3) 144.0
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 N1 C1 C8 -0.9(3) ?
C1 N1 C2 C3 179.8(3) ?
C1 N1 C2 C7 0.4(3) ?
N1 C2 C3 C4 -179.5(3) ?
C7 C2 C3 C4 -0.2(4) ?
C2 C3 C4 C5 -1.5(5) ?
C3 C4 C5 C6 1.9(5) ?
C4 C5 C6 C7 -0.4(5) ?
C5 C6 C7 C2 -1.2(4) ?
C5 C6 C7 C8 179.8(3) ?
N1 C2 C7 C6 -179.0(3) ?
C3 C2 C7 C6 1.5(4) ?
N1 C2 C7 C8 0.2(3) ?
C3 C2 C7 C8 -179.2(3) ?
N1 C1 C8 C9 178.3(3) ?
N1 C1 C8 C7 1.0(3) ?
C6 C7 C8 C1 178.4(3) ?
C2 C7 C8 C1 -0.7(3) ?
C6 C7 C8 C9 1.0(5) ?
C2 C7 C8 C9 -178.1(3) ?
C1 C8 C9 O1 -178.2(3) y
C7 C8 C9 O1 -1.3(5) ?
C1 C8 C9 C10 -1.4(4) ?
C7 C8 C9 C10 175.5(3) ?
O1 C9 C10 O2 -149.3(3) y
C8 C9 C10 O2 33.7(4) ?
O1 C9 C10 N2 30.4(4) ?
C8 C9 C10 N2 -146.6(3) ?
_cod_database_fobs_code 2018696