#------------------------------------------------------------------------------
#$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/42/2204222.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_2204222
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
'Kirsop, Peter'
'Storey, John M. D.'
'Harrison, William T. A.'
_publ_section_title
;
4-(3-Allyloxy-2-bromophenoxy)but-2-enenitrile
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o1636
_journal_page_last               o1638
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C13 H12 Br N O2'
_chemical_formula_moiety         'C13 H12 Br N O2'
_chemical_formula_sum            'C13 H12 Br N O2'
_chemical_formula_weight         294.15
_chemical_name_systematic
;
4-(3-Allyloxy-2-bromophenoxy)but-2-enenitrile
;
_symmetry_cell_setting           monoclinic
_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                 97.570(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.3681(3)
_cell_length_b                   19.1969(12)
_cell_length_c                   15.0270(9)
_cell_measurement_reflns_used    2721
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1249.09(14)
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
;
HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK and SORTAV (Blessing
1995)
;
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w'
_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  0.0893
_diffrn_reflns_av_sigmaI/netI    0.0682
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17155
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         3.46
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    3.280
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.577
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0550
_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^)+(0.0553P)^2^+1.5353P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1333
_reflns_number_gt                1930
_reflns_number_total             2871
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    sj6002.cif
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_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_
_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
C1A -0.584(2) 0.5535(5) -0.1148(5) 0.053(3) Uiso d P 0.710(19) A 1 C
H1A -0.4538 0.5683 -0.1570 0.064 Uiso calc PR 0.710(19) A 1 H
H2A -0.6442 0.5855 -0.0721 0.064 Uiso calc PR 0.710(19) A 1 H
C2A -0.685(2) 0.4863(5) -0.1156(5) 0.045(2) Uiso d P 0.710(19) A 1 C
H3A -0.8158 0.4715 -0.0734 0.055 Uiso calc PR 0.710(19) A 1 H
C1B -0.761(7) 0.5324(13) -0.1075(13) 0.067(7) Uiso d P 0.290(19) A 2 C
H1B -0.9639 0.5157 -0.1257 0.081 Uiso calc PR 0.290(19) A 2 H
H2B -0.7298 0.5738 -0.0729 0.081 Uiso calc PR 0.290(19) A 2 H
C2B -0.548(6) 0.5020(10) -0.1278(12) 0.049(6) Uiso d P 0.290(19) A 2 C
H3B -0.3460 0.5192 -0.1092 0.059 Uiso calc PR 0.290(19) A 2 H
C3 -0.5902(12) 0.4356(2) -0.1833(3) 0.0513(13) Uani d . 1 . . C
H4 -0.7735 0.4117 -0.2152 0.062 Uiso calc R 1 A 1 H
H5 -0.4821 0.4602 -0.2280 0.062 Uiso calc R 1 A 1 H
C4 -0.3122(10) 0.3282(2) -0.1780(3) 0.0383(10) Uani d . 1 . . C
C5 -0.4243(10) 0.3126(2) -0.2675(3) 0.0414(11) Uani d . 1 A . C
H6 -0.5650 0.3431 -0.3017 0.050 Uiso calc R 1 . . H
C6 -0.3282(10) 0.2524(2) -0.3053(3) 0.0423(11) Uani d . 1 . . C
H7 -0.4067 0.2419 -0.3658 0.051 Uiso calc R 1 A . H
C7 -0.1232(11) 0.2070(2) -0.2589(3) 0.0406(10) Uani d . 1 A . C
H8 -0.0598 0.1661 -0.2869 0.049 Uiso calc R 1 . . H
C8 -0.0092(10) 0.2221(2) -0.1696(3) 0.0372(10) Uani d . 1 . . C
C9 -0.1043(10) 0.2819(2) -0.1303(2) 0.0375(10) Uani d . 1 A . C
C10 0.2921(10) 0.1178(2) -0.1518(3) 0.0414(10) Uani d . 1 . . C
H9 0.3864 0.1264 -0.2072 0.050 Uiso calc R 1 A . H
H10 0.1121 0.0866 -0.1667 0.050 Uiso calc R 1 . . H
C11 0.5206(10) 0.0852(2) -0.0825(3) 0.0410(10) Uani d . 1 A . C
H11 0.5965 0.0402 -0.0946 0.049 Uiso calc R 1 . . H
C12 0.6251(10) 0.1146(2) -0.0052(3) 0.0433(11) Uani d . 1 . . C
H12 0.5542 0.1598 0.0077 0.052 Uiso calc R 1 A . H
C13 0.8433(11) 0.0801(2) 0.0602(3) 0.0434(11) Uani d . 1 A . C
N1 1.0142(10) 0.0530(2) 0.1137(3) 0.0545(11) Uani d . 1 . . N
O1 -0.3859(8) 0.38583(15) -0.13333(19) 0.0496(8) Uani d . 1 A . O
O2 0.1970(7) 0.18162(14) -0.11670(18) 0.0417(7) Uani d . 1 A . O
Br1 0.04780(12) 0.30109(2) -0.00932(3) 0.0501(2) Uani d . 1 . . Br
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
C3 0.075(3) 0.040(3) 0.036(2) 0.016(2) -0.004(2) 0.0093(19)
C4 0.049(3) 0.032(2) 0.033(2) -0.0029(19) 0.0029(19) 0.0066(17)
C5 0.049(3) 0.043(3) 0.031(2) -0.002(2) 0.0003(19) 0.0092(18)
C6 0.055(3) 0.040(3) 0.029(2) -0.010(2) -0.003(2) -0.0010(18)
C7 0.054(3) 0.035(2) 0.033(2) -0.008(2) 0.003(2) -0.0021(18)
C8 0.046(3) 0.033(2) 0.032(2) 0.0000(19) 0.0025(19) 0.0042(17)
C9 0.054(3) 0.040(2) 0.0168(18) -0.002(2) -0.0008(18) 0.0022(16)
C10 0.051(3) 0.031(2) 0.043(3) -0.003(2) 0.006(2) -0.0024(19)
C11 0.046(3) 0.032(2) 0.045(3) 0.0010(19) 0.006(2) -0.0039(19)
C12 0.046(3) 0.036(2) 0.046(3) 0.005(2) 0.002(2) 0.002(2)
C13 0.049(3) 0.040(3) 0.041(2) 0.005(2) 0.007(2) -0.011(2)
N1 0.063(3) 0.049(2) 0.048(2) 0.011(2) -0.006(2) -0.0121(19)
O1 0.076(2) 0.0384(18) 0.0312(15) 0.0182(16) -0.0038(15) 0.0020(13)
O2 0.0562(19) 0.0360(17) 0.0310(15) 0.0068(14) -0.0014(14) -0.0021(12)
Br1 0.0721(4) 0.0451(3) 0.0293(3) 0.0144(2) -0.0078(2) -0.00387(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1A C2A 1.362(17) ?
C1A H1A 0.9500 ?
C1A H2A 0.9500 ?
C2A C3 1.506(9) ?
C2A H3A 0.9500 ?
C1B C2B 1.17(4) ?
C1B H1B 0.9500 ?
C1B H2B 0.9500 ?
C2B C3 1.521(19) ?
C2B H3B 0.9500 ?
C3 O1 1.448(5) ?
C3 H4 0.9900 ?
C3 H5 0.9900 ?
C4 O1 1.354(5) ?
C4 C9 1.399(6) ?
C4 C5 1.403(6) ?
C5 C6 1.377(6) ?
C5 H6 0.9500 ?
C6 C7 1.372(6) ?
C6 H7 0.9500 ?
C7 C8 1.399(6) ?
C7 H8 0.9500 ?
C8 O2 1.364(5) ?
C8 C9 1.380(6) ?
C9 Br1 1.888(4) y
C10 O2 1.417(5) ?
C10 C11 1.483(6) ?
C10 H9 0.9900 ?
C10 H10 0.9900 ?
C11 C12 1.318(6) y
C11 H11 0.9500 ?
C12 C13 1.437(6) y
C12 H12 0.9500 ?
C13 N1 1.148(5) y
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2A C1A H1A 120.0
C2A C1A H2A 120.0
H1A C1A H2A 120.0
C1A C2A C3 120.0(9)
C1A C2A H3A 120.0
C3 C2A H3A 120.0
C2B C1B H1B 120.0
C2B C1B H2B 120.0
H1B C1B H2B 120.0
C1B C2B C3 121(3)
C1B C2B H3B 119.4
C3 C2B H3B 119.4
O1 C3 C2A 106.4(4)
O1 C3 C2B 104.4(8)
C2A C3 C2B 27.3(8)
O1 C3 H4 110.4
C2A C3 H4 110.4
C2B C3 H4 133.2
O1 C3 H5 110.4
C2A C3 H5 110.4
C2B C3 H5 86.5
H4 C3 H5 108.6
O1 C4 C9 116.5(4)
O1 C4 C5 125.1(4)
C9 C4 C5 118.4(4)
C6 C5 C4 119.3(4)
C6 C5 H6 120.4
C4 C5 H6 120.4
C7 C6 C5 122.5(4)
C7 C6 H7 118.8
C5 C6 H7 118.8
C6 C7 C8 118.8(4)
C6 C7 H8 120.6
C8 C7 H8 120.6
O2 C8 C9 116.0(3)
O2 C8 C7 124.4(4)
C9 C8 C7 119.6(4)
C8 C9 C4 121.4(4)
C8 C9 Br1 119.1(3)
C4 C9 Br1 119.5(3)
O2 C10 C11 107.9(3)
O2 C10 H9 110.1
C11 C10 H9 110.1
O2 C10 H10 110.1
C11 C10 H10 110.1
H9 C10 H10 108.4
C12 C11 C10 124.1(4)
C12 C11 H11 117.9
C10 C11 H11 117.9
C11 C12 C13 121.8(4)
C11 C12 H12 119.1
C13 C12 H12 119.1
N1 C13 C12 178.6(5)
C4 O1 C3 116.9(3)
C8 O2 C10 118.7(3)
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
C1A C2A C3 O1 111.3(7) y
C1A C2A C3 C2B 21.8(16) ?
C1B C2B C3 O1 -129.0(19) ?
C1B C2B C3 C2A -30.9(18) ?
O1 C4 C5 C6 179.3(4) ?
C9 C4 C5 C6 0.3(7) ?
C4 C5 C6 C7 -0.6(7) ?
C5 C6 C7 C8 0.5(7) ?
C6 C7 C8 O2 -179.4(4) ?
C6 C7 C8 C9 -0.1(7) ?
O2 C8 C9 C4 179.1(4) ?
C7 C8 C9 C4 -0.3(7) ?
O2 C8 C9 Br1 -1.3(5) ?
C7 C8 C9 Br1 179.3(3) ?
O1 C4 C9 C8 -179.0(4) ?
C5 C4 C9 C8 0.1(7) ?
O1 C4 C9 Br1 1.5(6) ?
C5 C4 C9 Br1 -179.4(3) ?
O2 C10 C11 C12 -4.0(6) y
C10 C11 C12 C13 179.0(4) y
C9 C4 O1 C3 177.4(4) ?
C5 C4 O1 C3 -1.7(7) ?
C2A C3 O1 C4 169.1(6) ?
C2B C3 O1 C4 -162.7(11) ?
C9 C8 O2 C10 177.0(4) ?
C7 C8 O2 C10 -3.6(6) ?
C11 C10 O2 C8 178.5(4) ?
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
C12 H12 O2 . 0.95 2.31 2.671(5) 102 y
C11 H11 N1 3_755 0.95 2.51 3.410(6) 158 y
_cod_database_code 2204222