#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/14/2011469.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_2011469
loop_
_publ_author_name
'Sakamoto, Jun'
'Nakagawa, Takashi'
'Kanehisa, Nobuko'
'Kai, Yasushi'
'Katsura, Masahiro'
_publ_section_title
;
 2-Phenylmalonamide
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e485
_journal_page_last               e486
_journal_paper_doi               10.1107/S0108270100011938
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C9 H10 N2 O2'
_chemical_formula_sum            'C9 H10 N2 O2'
_chemical_formula_weight         178.19
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 104.100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.079(2)
_cell_length_b                   7.555(2)
_cell_length_c                   13.015(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      14.6
_cell_volume                     865.8(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
 1990)
;
_computing_data_reduction
;
TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 1999)
;
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_measured_fraction_theta_full .9990
_diffrn_measured_fraction_theta_max .9990
_diffrn_measurement_device_type  'Rigaku AFC-5R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .7107
_diffrn_reflns_av_R_equivalents  .016
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2275
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_standards_decay_%        2.00
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          .20
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .10
_refine_diff_density_max         .54
_refine_diff_density_min         -.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.231
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1658
_refine_ls_R_factor_gt           .0378
_refine_ls_shift/su_max          .0039
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + {0.050[Max(Fo²,0) + 2Fc²]/3}²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1043
_reflns_number_gt                1347
_reflns_number_total             1994
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qd0028.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2011469
_cod_database_fobs_code          2011469
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,1/2-y,1/2+z
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O(1) -.39870(10) -.0458(2) .14484(9) .0421(3) Uani d . 1.00 . . O
O(2) -.06500(10) -.2840(2) .01448(8) .0380(3) Uani d . 1.00 . . O
N(1) -.3087(2) -.0668(2) -.00080(10) .0449(4) Uani d . 1.00 . . N
N(2) -.0672(2) -.4955(2) .13540(10) .0386(4) Uani d . 1.00 . . N
C(1) -.3028(2) -.0996(2) .09980(10) .0294(4) Uani d . 1.00 . . C
C(2) -.1680(2) -.2077(2) .16340(10) .0276(4) Uani d . 1.00 . . C
C(3) -.0958(2) -.3331(2) .09750(10) .0289(4) Uani d . 1.00 . . C
C(4) -.0465(2) -.0843(2) .22790(10) .0294(4) Uani d . 1.00 . . C
C(5) -.0096(2) -.0941(3) .33740(10) .0403(5) Uani d . 1.00 . . C
C(6) .1028(2) .0151(3) .39680(10) .0495(5) Uani d . 1.00 . . C
C(7) .1798(2) .1326(3) .3481(2) .0484(5) Uani d . 1.00 . . C
C(8) .1430(2) .1433(3) .2385(2) .0473(5) Uani d . 1.00 . . C
C(9) .0297(2) .0362(2) .17900(10) .0396(5) Uani d . 1.00 . . C
H(1) -.063(2) -.183(3) .3720(10) .046(5) Uiso calc . 1.00 . . H
H(2) .130(3) .006(3) .472(2) .058(6) Uiso calc . 1.00 . . H
H(3) .262(3) .208(3) .393(2) .069(7) Uiso calc . 1.00 . . H
H(4) .201(2) .228(3) .202(2) .060(6) Uiso calc . 1.00 . . H
H(5) .004(2) .044(3) .100(2) .055(6) Uiso calc . 1.00 . . H
H(6) -.241(3) -.112(3) -.030(2) .067(7) Uiso calc . 1.00 . . H
H(7) -.388(3) -.018(3) -.039(2) .059(6) Uiso calc . 1.00 . . H
H(8) -.023(2) -.573(3) .098(2) .047(5) Uiso calc . 1.00 . . H
H(9) -.084(2) -.529(2) .202(2) .046(5) Uiso calc . 1.00 . . H
H(10) -.208(2) -.276(2) .2100(10) .026(4) Uiso calc . 1.00 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .003 .002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H .000 .000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O .011 .006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N .006 .003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C(1) N(1) H(6) 1_555 1_555 119.0(10) no
C(1) N(1) H(7) 1_555 1_555 119.0(10) no
H(6) N(1) H(7) 1_555 1_555 119(2) no
C(3) N(2) H(8) 1_555 1_555 118.0(10) no
C(3) N(2) H(9) 1_555 1_555 121.0(10) no
H(8) N(2) H(9) 1_555 1_555 119.0(10) no
O(1) C(1) N(1) 1_555 1_555 123.20(10) no
O(1) C(1) C(2) 1_555 1_555 118.90(10) no
N(1) C(1) C(2) 1_555 1_555 117.90(10) no
C(1) C(2) C(3) 1_555 1_555 115.00(10) yes
C(1) C(2) C(4) 1_555 1_555 110.20(10) no
C(1) C(2) H(10) 1_555 1_555 104.9(9) no
C(3) C(2) C(4) 1_555 1_555 109.60(10) no
C(3) C(2) H(10) 1_555 1_555 108.2(10) no
C(4) C(2) H(10) 1_555 1_555 108.7(9) no
O(2) C(3) N(2) 1_555 1_555 122.50(10) no
O(2) C(3) C(2) 1_555 1_555 121.60(10) no
N(2) C(3) C(2) 1_555 1_555 115.90(10) no
C(2) C(4) C(5) 1_555 1_555 119.60(10) no
C(2) C(4) C(9) 1_555 1_555 121.40(10) no
C(5) C(4) C(9) 1_555 1_555 119.0(2) no
C(4) C(5) C(6) 1_555 1_555 120.1(2) no
C(4) C(5) H(1) 1_555 1_555 118.0(10) no
C(6) C(5) H(1) 1_555 1_555 121.0(10) no
C(5) C(6) C(7) 1_555 1_555 120.9(2) no
C(5) C(6) H(2) 1_555 1_555 120.0(10) no
C(7) C(6) H(2) 1_555 1_555 119.0(10) no
C(6) C(7) C(8) 1_555 1_555 119.3(2) no
C(6) C(7) H(3) 1_555 1_555 119.0(10) no
C(8) C(7) H(3) 1_555 1_555 121.0(10) no
C(7) C(8) C(9) 1_555 1_555 120.1(2) no
C(7) C(8) H(4) 1_555 1_555 119.0(10) no
C(9) C(8) H(4) 1_555 1_555 120.0(10) no
C(4) C(9) C(8) 1_555 1_555 120.7(2) no
C(4) C(9) H(5) 1_555 1_555 119.0(10) no
C(8) C(9) H(5) 1_555 1_555 119.0(10) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(1) . . 1.230(2) yes
O(2) C(3) . . 1.237(2) yes
N(1) C(1) . . 1.321(2) yes
N(1) H(6) . . .87(2) no
N(1) H(7) . . .85(2) no
N(2) C(3) . . 1.324(2) yes
N(2) H(8) . . .91(2) no
N(2) H(9) . . .94(2) no
C(1) C(2) . . 1.535(2) yes
C(2) C(3) . . 1.528(2) yes
C(2) C(4) . . 1.530(2) yes
C(2) H(10) . . .94(2) no
C(4) C(5) . . 1.384(2) no
C(4) C(9) . . 1.388(2) no
C(5) C(6) . . 1.391(3) no
C(5) H(1) . . 1.00(2) no
C(6) C(7) . . 1.376(3) no
C(6) H(2) . . .96(2) no
C(7) C(8) . . 1.385(3) no
C(7) H(3) . . 1.00(2) no
C(8) C(9) . . 1.388(3) no
C(8) H(4) . . 1.02(2) no
C(9) H(5) . . 1.00(2) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) H(1) 2.76(2) 2_455
O(1) H(10) 2.79(2) 2_455
O(1) N(2) 2.975(2) 2_455
O(1) N(1) 2.978(2) 3_455
O(1) H(6) 3.46(2) 3_455
O(1) C(2) 3.520(2) 2_455
O(1) C(5) 3.534(2) 2_455
O(1) C(7) 3.541(2) 2_445
O(1) H(8) 3.59(2) 2_455
O(2) H(3) 2.72(2) 2_545
O(2) H(4) 2.82(2) 3_555
O(2) N(2) 3.027(2) 3_545
O(2) H(2) 3.17(2) 4_444
O(2) C(9) 3.216(2) 3_555
O(2) C(8) 3.367(2) 3_555
O(2) C(6) 3.498(2) 4_444
O(2) O(2) 3.522(2) 3_545
O(2) C(7) 3.575(2) 2_545
N(1) H(7) 3.00(2) 3_455
N(1) H(1) 3.13(2) 4_444
N(1) H(3) 3.18(2) 4_454
N(1) H(4) 3.24(2) 3_555
N(1) H(5) 3.33(2) 3_555
N(1) H(2) 3.37(2) 4_444
N(1) C(5) 3.529(3) 4_444
N(2) H(2) 3.04(2) 4_444
N(2) H(4) 3.17(2) 1_545
N(2) H(3) 3.27(2) 2_545
N(2) H(8) 3.38(2) 3_545
N(2) C(8) 3.412(3) 1_545
N(2) H(3) 3.54(2) 4_444
N(2) H(5) 3.59(2) 1_545
C(1) H(7) 2.87(2) 3_455
C(1) H(9) 3.05(2) 2_455
C(1) H(1) 3.42(2) 2_455
C(1) H(10) 3.46(2) 2_455
C(1) H(2) 3.47(2) 4_444
C(2) H(9) 3.45(2) 2_455
C(2) H(2) 3.52(2) 4_444
C(3) H(2) 2.93(2) 4_444
C(3) H(3) 3.02(2) 2_545
C(3) H(8) 3.09(2) 3_545
C(3) C(6) 3.567(2) 4_444
C(4) H(4) 3.36(2) 2_545
C(4) H(10) 3.45(2) 2_455
C(5) H(2) 3.02(2) 3_556
C(5) H(4) 3.25(2) 2_545
C(5) H(7) 3.40(2) 4_545
C(5) H(6) 3.44(2) 4_545
C(5) H(10) 3.46(2) 2_455
C(6) H(2) 3.03(2) 3_556
C(6) H(4) 3.26(2) 2_545
C(6) H(1) 3.37(2) 3_556
C(6) H(6) 3.40(2) 4_545
C(7) H(4) 3.36(2) 2_545
C(7) H(7) 3.38(2) 4_555
C(7) H(8) 3.40(2) 2_555
C(8) H(8) 2.98(2) 1_565
C(8) H(6) 3.07(2) 3_555
C(8) H(9) 3.18(2) 1_565
C(8) H(4) 3.45(2) 2_545
C(9) H(6) 3.10(2) 3_555
C(9) H(8) 3.13(2) 1_565
C(9) H(3) 3.39(2) 2_545
C(9) H(4) 3.46(2) 2_545
C(9) H(9) 3.48(2) 1_565
H(1) H(2) 2.62(3) 3_556
H(1) H(7) 2.84(3) 4_545
H(1) H(6) 3.28(3) 4_545
H(1) H(9) 3.32(3) 2_455
H(1) H(7) 3.44(3) 2_445
H(2) H(2) 2.63(4) 3_556
H(2) H(6) 3.20(3) 4_545
H(2) H(8) 3.21(3) 4_545
H(2) H(9) 3.45(3) 4_545
H(2) H(10) 3.54(3) 4_545
H(3) H(7) 2.95(3) 4_555
H(3) H(8) 3.08(3) 4_545
H(3) H(8) 3.16(3) 2_555
H(3) H(6) 3.21(3) 4_555
H(3) H(5) 3.30(3) 2_555
H(3) H(5) 3.57(3) 4_555
H(4) H(6) 2.51(3) 3_555
H(4) H(8) 2.63(3) 1_565
H(4) H(9) 3.17(3) 1_565
H(4) H(7) 3.40(3) 3_555
H(5) H(6) 2.59(3) 3_555
H(5) H(5) 2.68(4) 3_555
H(5) H(8) 2.90(3) 1_565
H(7) H(7) 2.51(5) 3_455
H(7) H(9) 3.43(3) 4_444
H(8) H(8) 2.91(4) 3_545
H(9) H(10) 3.07(3) 2_445
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
_geom_hbond_publ_flag
N1 H6 O2 . .87(3) 2.03(3) 2.723(2) 136(2) yes
N1 H7 O1 3_455 .85(3) 2.14(3) 2.978(2) 167(2) yes
N2 H8 O2 3_545 .91(2) 2.13(2) 3.027(2) 168(2) yes
N2 H9 O1 2_445 .95(2) 2.04(2) 2.9753(19) 167.1(15) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O(1) C(1) C(2) C(3) 1_555 1_555 1_555 1_555 154.60(10) no
O(1) C(1) C(2) C(4) 1_555 1_555 1_555 1_555 -80.9(2) no
O(2) C(3) C(2) C(1) 1_555 1_555 1_555 1_555 46.6(2) no
O(2) C(3) C(2) C(4) 1_555 1_555 1_555 1_555 -78.2(2) no
N(1) C(1) C(2) C(3) 1_555 1_555 1_555 1_555 -26.2(2) no
N(1) C(1) C(2) C(4) 1_555 1_555 1_555 1_555 98.2(2) no
N(2) C(3) C(2) C(1) 1_555 1_555 1_555 1_555 -134.10(10) no
N(2) C(3) C(2) C(4) 1_555 1_555 1_555 1_555 101.1(2) no
C(1) C(2) C(4) C(5) 1_555 1_555 1_555 1_555 117.3(2) no
C(1) C(2) C(4) C(9) 1_555 1_555 1_555 1_555 -63.7(2) no
C(2) C(4) C(5) C(6) 1_555 1_555 1_555 1_555 178.7(2) no
C(2) C(4) C(9) C(8) 1_555 1_555 1_555 1_555 -178.0(2) no
C(3) C(2) C(4) C(5) 1_555 1_555 1_555 1_555 -115.30(10) no
C(3) C(2) C(4) C(9) 1_555 1_555 1_555 1_555 63.8(2) no
C(4) C(5) C(6) C(7) 1_555 1_555 1_555 1_555 -.6(3) no
C(4) C(9) C(8) C(7) 1_555 1_555 1_555 1_555 -.9(3) no
C(5) C(4) C(9) C(8) 1_555 1_555 1_555 1_555 1.1(3) no
C(5) C(6) C(7) C(8) 1_555 1_555 1_555 1_555 .8(3) no
C(6) C(5) C(4) C(9) 1_555 1_555 1_555 1_555 -.3(2) no
C(6) C(7) C(8) C(9) 1_555 1_555 1_555 1_555 .0(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2028984
