#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011356.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_2011356
loop_
_publ_author_name
'Sakamoto, Jun'
'Nakagawa, Takashi'
'Kanehisa, Nobuko'
'Kai, Yasushi'
'Katsura, Masahiro'
_publ_section_title
;
 3-Chloropropionamide
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e413
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C3 H6 Cl N O'
_chemical_formula_sum            'C3 H6 Cl N O'
_chemical_formula_weight         107.54
_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'
_cell_angle_alpha                90
_cell_angle_beta                 105.590(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.880(2)
_cell_length_b                   8.201(3)
_cell_length_c                   9.298(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      14.2
_cell_volume                     505.3(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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku AFC-5R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .7107
_diffrn_reflns_av_R_equivalents  .007
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1306
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_standards_decay_%        3.9
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .609
_exptl_absorpt_correction_T_max  .913
_exptl_absorpt_correction_T_min  .882
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          .20
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .15
_refine_diff_density_max         .22
_refine_diff_density_min         -.20
_refine_ls_extinction_coef       .010(10)
_refine_ls_extinction_method     'Zachariasen(1967) type 2 Gaussian isotropic'
_refine_ls_goodness_of_fit_ref   .960
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     80
_refine_ls_number_reflns         849
_refine_ls_R_factor_gt           .0354
_refine_ls_shift/su_max          .0065
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/{\s^2^(Fo^2^) + [0.08600(Max(Fo^2^,0) + 2Fc^2^)/3]^2^}'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1085
_reflns_number_gt                757
_reflns_number_total             1153
_reflns_threshold_expression     F^2^>2\s(F^2^)
_[local]_cod_data_source_file    qa0373.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_original_cell_volume        505.3(2)
_cod_database_code               2011356
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
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_occupancy
_atom_site_type_symbol
Cl(1) .13036(9) .23613(9) .61173(8) .0644(2) Uani d 1.00 Cl
O(1) -.3580(2) .1309(2) .6592(2) .0406(4) Uani d 1.00 O
N(1) -.4319(3) .1839(3) .4135(2) .0468(5) Uani d 1.00 N
C(1) -.3467(3) .2198(2) .5548(2) .0345(5) Uani d 1.00 C
C(2) -.2344(4) .3796(3) .5838(3) .0476(6) Uani d 1.00 C
C(3) -.0272(4) .3611(3) .6918(3) .0525(7) Uani d 1.00 C
H(1) -.409(4) .249(3) .348(3) .050(7) Uiso calc 1.00 H
H(2) -.504(4) .098(4) .388(3) .058(7) Uiso calc 1.00 H
H(3) .037(4) .462(4) .717(3) .075(8) Uiso calc 1.00 H
H(4) -.038(4) .302(3) .786(3) .052(7) Uiso calc 1.00 H
H(5) -.230(4) .431(4) .493(3) .058(7) Uiso calc 1.00 H
H(6) -.310(4) .456(4) .632(3) .061(7) Uiso calc 1.00 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
Cl(1) .0507(4) .0737(5) .0666(5) -.0013(3) .0121(3) .0024(3)
O(1) .0503(8) .0399(8) .0304(7) -.0066(6) .0085(6) .0015(6)
N(1) .0560(10) .0520(10) .0292(10) -.0139(9) .0058(8) .0030(9)
C(1) .0331(9) .0360(9) .0340(10) .0011(8) .0075(8) .0009(8)
C(2) .0570(10) .0330(10) .0500(10) -.0049(10) .0080(10) .0007(9)
C(3) .0550(10) .0530(10) .0460(10) -.0200(10) .0070(10) -.0080(10)
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)
;
Cl Cl .148 .159
;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(1) 1_555 1_555 116.0(10) no
C(1) N(1) H(2) 1_555 1_555 121.0(10) no
H(1) N(1) H(2) 1_555 1_555 121(2) no
O(1) C(1) N(1) 1_555 1_555 123.2(2) no
O(1) C(1) C(2) 1_555 1_555 120.7(2) no
N(1) C(1) C(2) 1_555 1_555 116.1(2) no
C(1) C(2) C(3) 1_555 1_555 112.2(2) no
C(1) C(2) H(5) 1_555 1_555 111.0(10) no
C(1) C(2) H(6) 1_555 1_555 108.0(10) no
C(3) C(2) H(5) 1_555 1_555 112.0(10) no
C(3) C(2) H(6) 1_555 1_555 106.0(10) no
H(5) C(2) H(6) 1_555 1_555 105(2) no
Cl(1) C(3) C(2) 1_555 1_555 110.4(2) no
Cl(1) C(3) H(3) 1_555 1_555 108.0(10) no
Cl(1) C(3) H(4) 1_555 1_555 105.0(10) no
C(2) C(3) H(3) 1_555 1_555 111.0(10) no
C(2) C(3) H(4) 1_555 1_555 110.0(10) no
H(3) C(3) H(4) 1_555 1_555 109(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl(1) C(3) 1.793(3) no
O(1) C(1) 1.233(3) no
N(1) C(1) 1.320(3) no
N(1) H(1) .85(3) no
N(1) H(2) .86(3) no
C(1) C(2) 1.508(3) no
C(2) C(3) 1.515(3) no
C(2) H(5) .95(3) no
C(2) H(6) .99(3) no
C(3) H(3) .94(3) no
C(3) H(4) 1.03(3) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
Cl(1) H(4) 2.95(3) 4_554
Cl(1) H(5) 3.04(3) 3_566
Cl(1) H(3) 3.14(3) 2_546
Cl(1) H(6) 3.30(3) 2_546
Cl(1) H(1) 3.34(3) 4_655
Cl(1) H(2) 3.36(3) 4_655
Cl(1) O(1) 3.535(2) 1_655
Cl(1) N(1) 3.582(2) 4_655
O(1) H(3) 2.60(3) 2_546
O(1) N(1) 2.947(3) 3_456
O(1) N(1) 2.966(3) 4_555
O(1) H(5) 3.04(3) 4_555
O(1) H(2) 3.41(3) 4_555
O(1) C(3) 3.444(3) 2_546
O(1) H(1) 3.50(3) 3_456
N(1) H(2) 3.06(3) 3_456
N(1) H(6) 3.17(3) 4_554
N(1) H(4) 3.24(3) 4_554
N(1) H(6) 3.41(3) 3_466
C(1) H(1) 2.89(3) 4_555
C(1) H(2) 2.90(3) 3_456
C(1) H(3) 3.33(3) 2_546
C(2) H(1) 3.19(3) 4_555
C(2) H(6) 3.50(3) 3_466
C(3) H(5) 3.26(3) 3_566
C(3) H(3) 3.38(3) 2_546
C(3) H(1) 3.45(3) 4_555
C(3) H(2) 3.59(3) 4_655
H(1) H(4) 2.80(4) 4_554
H(1) H(6) 2.84(4) 4_554
H(1) H(6) 3.13(4) 3_466
H(1) H(2) 3.56(4) 2_455
H(2) H(2) 2.61(6) 3_456
H(2) H(6) 3.07(4) 4_554
H(2) H(3) 3.17(4) 4_454
H(3) H(4) 2.78(4) 2_556
H(3) H(5) 2.79(4) 3_566
H(4) H(5) 3.24(4) 4_555
H(5) H(6) 3.20(4) 3_466
H(5) H(5) 3.33(5) 3_566
H(6) H(6) 3.15(5) 3_466
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 H1 O1 4_554 .86(3) 2.12(3) 2.967(3) 169(2) no
N1 H2 O1 3_456 .86(3) 2.10(3) 2.947(3) 172(3) no
C3 H3 O1 2_556 .94(3) 2.60(3) 3.445(3) 150(2) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cl(1) C(3) C(2) C(1) 1_555 1_555 1_555 1_555 65.2(3) no
O(1) C(1) C(2) C(3) 1_555 1_555 1_555 1_555 48.6(3) no
N(1) C(1) C(2) C(3) 1_555 1_555 1_555 1_555 -132.2(2) no