#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006627.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_2006627
loop_
_publ_author_name
'Warrener, R. N.'
'Maksimovic, L.'
'Kennard, C. H. L.'
_publ_section_title
;
 (1\a,2\b,3\a,6\a,7\b,8\a,9\b,13\b)-9,13-Dibromo-11-methyl-14,15-dioxa-11-azapentacyclo[6.5.1.1^3,6^.0^2,7^.0^9,13^]pentadec-4-ene-10,12-dione
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1501
_journal_page_last               1502
_journal_volume                  53
_journal_year                    1997
_chemical_formula_structural     'C13 H11 Br2 N O4'
_chemical_formula_sum            'C13 H11 Br2 N O4'
_chemical_formula_weight         405.05
_chemical_melting_point          519(3)
_chemical_name_systematic
;
(1\a,2\b,3\a,6\a,7\b,8\a,9\b,13\b)-9,13-dibromo-11-methyl-11-aza-
14,15-dioxa-11-pentacyclo [6.5.1.1^3,6^.0^2,7^.0^9,13^]
pentadec-4-en-10,12-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 95.314(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3770(10)
_cell_length_b                   18.664(3)
_cell_length_c                   9.897(2)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      6
_cell_volume                     1356.8(4)
_computing_cell_refinement       SDP-Plus
_computing_data_collection       'SDP-Plus (Frenz, 1985)'
_computing_data_reduction
'Xtal3.2 DIFDAT (Hall, Flack & Stewart, 1992)'
_computing_molecular_graphics    'PLATON96 (Spek, 1996)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      298(2)
_diffrn_measurement_device       'CAD4 MicroVAX-controlled'
_diffrn_measurement_method       2\q/\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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3412
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 250
_diffrn_standards_interval_time  '2 hours'
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.986
_exptl_absorpt_correction_T_max  0.52
_exptl_absorpt_correction_T_min  0.21
_exptl_absorpt_correction_type
;
empirical \y scan (North, Phillips & Mathews, 1968)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.983
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.958
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.025
_refine_ls_goodness_of_fit_obs   1.098
_refine_ls_hydrogen_treatment
;
hydrogen atoms in calculated positions, but not refined
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3411
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_restrained_S_obs      1.098
_refine_ls_R_factor_all          0.116
_refine_ls_R_factor_obs          0.047
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0697P)^2^+1.0814P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.139
_refine_ls_wR_factor_obs         0.110
_reflns_number_observed          1913
_reflns_number_total             3412
_reflns_observed_criterion       '>2 sigma(I)'
_[local]_cod_data_source_file    ta1163.cif
_[local]_cod_data_source_block   571rw3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '243-248\%C' was changed to '519(3)'
- it was converted from degrees Celsius(C) to Kelvins(K), the average
value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2006627
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_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
C1 0.032(3) 0.046(3) 0.038(3) -0.005(2) 0.017(2) -0.007(2)
C2 0.040(3) 0.041(2) 0.033(2) -0.009(2) 0.011(2) -0.002(2)
C3 0.045(3) 0.060(3) 0.033(3) -0.010(2) 0.013(2) -0.007(2)
C4 0.066(4) 0.066(3) 0.032(3) -0.014(3) -0.004(3) 0.004(2)
C5 0.047(3) 0.066(3) 0.050(3) -0.005(3) -0.005(3) 0.002(3)
C6 0.028(3) 0.054(3) 0.039(3) -0.005(2) 0.005(2) 0.000(2)
C7 0.030(2) 0.041(2) 0.032(2) -0.003(2) 0.008(2) 0.000(2)
C8 0.030(2) 0.035(2) 0.033(2) -0.001(2) 0.011(2) 0.000(2)
C9 0.030(2) 0.036(2) 0.030(2) 0.005(2) 0.010(2) -0.002(2)
Br9 0.0574(4) 0.0481(3) 0.0555(4) 0.0166(2) 0.0064(3) -0.0162(2)
C10 0.057(3) 0.036(2) 0.028(2) 0.000(2) 0.004(2) 0.001(2)
O10 0.076(3) 0.075(3) 0.035(2) -0.016(2) 0.014(2) 0.007(2)
N11 0.049(3) 0.042(2) 0.043(2) 0.009(2) -0.009(2) -0.004(2)
C11 0.088(5) 0.071(4) 0.070(5) 0.020(4) -0.031(4) -0.001(3)
C12 0.033(3) 0.054(3) 0.056(3) 0.001(2) 0.000(2) -0.022(3)
O12 0.034(2) 0.121(4) 0.077(3) 0.017(2) 0.002(2) -0.034(3)
C13 0.032(3) 0.041(2) 0.039(3) -0.005(2) 0.008(2) -0.006(2)
Br13 0.0751(5) 0.0673(4) 0.0544(4) -0.0393(3) 0.0141(3) -0.0003(3)
O14 0.036(2) 0.034(2) 0.035(2) 0.0009(13) 0.0085(14) -0.0045(13)
O15 0.045(2) 0.046(2) 0.042(2) -0.010(2) 0.009(2) -0.006(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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 0.4158(6) 0.8490(2) 0.1597(5) 0.0377(11) Uani d . 1 C
H1 0.5186(6) 0.8280(2) 0.1179(5) 0.047 Uiso calc R 1 H
C2 0.2731(6) 0.8823(2) 0.0581(4) 0.0377(10) Uani d . 1 C
H2 0.3063(6) 0.9307(2) 0.0307(4) 0.047 Uiso calc R 1 H
C3 0.2037(7) 0.8346(3) -0.0648(5) 0.0457(13) Uani d . 1 C
H3 0.2989(7) 0.8142(3) -0.1160(5) 0.057 Uiso calc R 1 H
C4 0.0638(8) 0.8793(3) -0.1464(5) 0.0550(14) Uani d . 1 C
H4 0.0763(8) 0.9017(3) -0.2291(5) 0.069 Uiso calc R 1 H
C5 -0.0802(8) 0.8805(3) -0.0771(6) 0.0550(14) Uani d . 1 C
H5 -0.1896(8) 0.9043(3) -0.0997(6) 0.069 Uiso calc R 1 H
C6 -0.0300(6) 0.8346(3) 0.0475(5) 0.0403(11) Uani d . 1 C
H6 -0.1330(6) 0.8145(3) 0.0906(5) 0.050 Uiso calc R 1 H
C7 0.1031(6) 0.8819(2) 0.1412(4) 0.0341(10) Uani d . 1 C
H7 0.0551(6) 0.9300(2) 0.1547(4) 0.043 Uiso calc R 1 H
C8 0.1790(6) 0.8469(2) 0.2733(4) 0.0321(10) Uani d . 1 C
H8 0.0862(6) 0.8242(2) 0.3236(4) 0.040 Uiso calc R 1 H
C9 0.3030(6) 0.8995(2) 0.3587(4) 0.0314(9) Uani d . 1 C
Br9 0.18821(7) 0.98851(3) 0.39964(6) 0.0536(2) Uani d . 1 Br
C10 0.3707(7) 0.8654(2) 0.4933(5) 0.0403(11) Uani d . 1 C
O10 0.2807(6) 0.8513(2) 0.5856(3) 0.0617(11) Uani d . 1 O
N11 0.5524(6) 0.8515(2) 0.4927(4) 0.0456(10) Uani d . 1 N
C11 0.6579(9) 0.8174(3) 0.6084(7) 0.079(2) Uani d . 1 C
H11A 0.7851(10) 0.819(2) 0.595(2) 0.098 Uiso calc R 1 H
H11B 0.620(4) 0.7685(8) 0.616(3) 0.098 Uiso calc R 1 H
H11C 0.638(5) 0.8426(15) 0.6902(9) 0.098 Uiso calc R 1 H
C12 0.6225(7) 0.8696(3) 0.3737(6) 0.0482(13) Uani d . 1 C
O12 0.7790(5) 0.8599(3) 0.3513(5) 0.0775(14) Uani d . 1 O
C13 0.4738(6) 0.9015(2) 0.2776(5) 0.0370(10) Uani d . 1 C
Br13 0.55889(9) 0.99312(3) 0.21972(6) 0.0651(2) Uani d . 1 Br
O14 0.3163(4) 0.79805(15) 0.2336(3) 0.0351(7) Uani d . 1 O
O15 0.0909(5) 0.7831(2) -0.0040(3) 0.0441(8) Uani d . 1 O
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
_geom_angle_publ_flag
O14 C1 C2 104.6(3) y
O14 C1 C13 98.8(3) ?
C2 C1 C13 111.4(4) ?
C1 C2 C3 116.1(4) ?
C1 C2 C7 101.0(3) ?
C3 C2 C7 100.7(3) ?
O15 C3 C4 101.6(4) ?
O15 C3 C2 102.5(3) ?
C4 C3 C2 105.2(4) ?
C5 C4 C3 106.0(5) ?
C4 C5 C6 105.4(5) y
O15 C6 C5 101.7(4) y
O15 C6 C7 102.2(4) y
C5 C6 C7 104.9(4) y
C8 C7 C6 115.5(4) y
C8 C7 C2 101.8(4) y
C6 C7 C2 100.5(3) y
O14 C8 C7 104.4(3) y
O14 C8 C9 99.0(3) y
C7 C8 C9 110.6(3) y
C10 C9 C8 110.2(4) y
C10 C9 C13 104.3(4) y
C8 C9 C13 101.6(3) y
C10 C9 Br9 107.0(3) y
C8 C9 Br9 114.5(3) y
C13 C9 Br9 118.7(3) y
O10 C10 N11 124.8(5) y
O10 C10 C9 126.6(5) y
N11 C10 C9 108.6(4) y
C10 N11 C12 113.9(4) y
C10 N11 C11 121.9(5) y
C12 N11 C11 124.2(5) y
O12 C12 N11 124.2(5) y
O12 C12 C13 126.5(5) y
N11 C12 C13 109.2(4) y
C12 C13 C1 111.0(4) y
C12 C13 C9 104.0(4) y
C1 C13 C9 101.1(3) y
C12 C13 Br13 107.5(3) y
C1 C13 Br13 114.3(3) y
C9 C13 Br13 118.5(3) y
C1 O14 C8 97.1(3) y
C6 O15 C3 95.9(3) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O14 1.441(5) y
C1 C2 1.520(7) y
C1 C13 1.554(6) y
C2 C3 1.556(6) y
C2 C7 1.562(6) y
C3 O15 1.439(6) y
C3 C4 1.505(7) y
C4 C5 1.317(8) y
C5 C6 1.518(7) y
C6 O15 1.437(6) y
C6 C7 1.559(6) y
C7 C8 1.521(6) y
C8 O14 1.445(5) y
C8 C9 1.540(6) y
C9 C10 1.519(6) y
C9 C13 1.556(6) y
C9 Br9 1.925(4) y
C10 O10 1.207(6) y
C10 N11 1.366(7) y
N11 C12 1.372(7) y
N11 C11 1.468(7) y
C12 O12 1.209(6) y
C12 C13 1.506(7) y
C13 Br13 1.926(4) y