#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:05:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180373 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/42/7204233.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7204233
loop_
_publ_author_name
'Alves, M. José'
'Azoia, Nuno G.'
'Bickley, Jamie F.'
'Fortes, A. Gil'
'Gilchrist, Thomas L.'
'Mendonça, Ricardo'
_publ_section_title
;
 Diels--Alder reactions of alkyl 2H-azirine-3-carboxylates with furans
;
_journal_issue                   22
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2969
_journal_paper_doi               10.1039/b106985n
_journal_year                    2001
_chemical_formula_sum            'C14 H11 Cl2 N O3'
_chemical_formula_weight         312.14
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 117.72(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.731(13)
_cell_length_b                   8.372(4)
_cell_length_c                   19.99(3)
_cell_measurement_temperature    213(2)
_cell_volume                     2775(6)
_computing_data_collection       'IPDS (STOE, 1997)'
_computing_data_reduction        'X-RED (STOE, 1996)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'Image Plate'
_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  0.0952
_diffrn_reflns_av_sigmaI/netI    0.0989
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7830
_diffrn_reflns_theta_full        24.05
_diffrn_reflns_theta_max         24.05
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.473
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.762
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.762
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0441
_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/[σ²(Fo²)+(0.0475P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                890
_reflns_number_total             2145
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b106985n.txt
_cod_data_source_block           amf01
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        2774(5)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7204233
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0338(3) 0.2707(6) 0.5252(2) 0.0657(12) Uani 1 1 d . . .
C2 C -0.0347(3) 0.1898(6) 0.5137(3) 0.0799(15) Uani 1 1 d . . .
H2 H -0.0632 0.1270 0.4703 0.096 Uiso 1 1 calc R . .
C3 C -0.0609(3) 0.2037(7) 0.5686(3) 0.0859(17) Uani 1 1 d . . .
H3 H -0.1067 0.1467 0.5626 0.103 Uiso 1 1 calc R . .
C4 C -0.0206(3) 0.2996(7) 0.6315(3) 0.0821(16) Uani 1 1 d . . .
H4 H -0.0394 0.3087 0.6676 0.099 Uiso 1 1 calc R . .
C5 C 0.0468(3) 0.3812(6) 0.6408(2) 0.0699(13) Uani 1 1 d . . .
C6 C 0.0794(2) 0.3647(6) 0.5899(2) 0.0606(12) Uani 1 1 d . . .
C7 C 0.1561(3) 0.4386(6) 0.6025(2) 0.0648(12) Uani 1 1 d . . .
H7 H 0.1515 0.5419 0.5766 0.078 Uiso 1 1 calc R . .
C8 C 0.2293(2) 0.3382(6) 0.6171(2) 0.0541(11) Uani 1 1 d . . .
C9 C 0.2977(3) 0.4237(6) 0.6098(2) 0.0664(13) Uani 1 1 d . . .
H9 H 0.3009 0.4040 0.5624 0.080 Uiso 1 1 calc R . .
C10 C 0.3731(3) 0.3823(6) 0.6831(3) 0.0714(13) Uani 1 1 d . . .
H10 H 0.4154 0.3138 0.6889 0.086 Uiso 1 1 calc R . .
C11 C 0.3662(3) 0.4641(6) 0.7373(3) 0.0761(14) Uani 1 1 d . . .
H11 H 0.404(3) 0.472(6) 0.790(3) 0.091 Uiso 1 1 d . . .
C12 C 0.2873(3) 0.5500(6) 0.6974(2) 0.0730(14) Uani 1 1 d . . .
H12 H 0.2822 0.6448 0.7245 0.088 Uiso 1 1 calc R . .
C13 C 0.2252(3) 0.1632(6) 0.6171(2) 0.0611(12) Uani 1 1 d . . .
C14 C 0.2747(3) -0.0708(6) 0.5870(3) 0.0835(15) Uani 1 1 d . . .
H14A H 0.3096 -0.1050 0.5660 0.100 Uiso 1 1 calc R . .
H14B H 0.2206 -0.1112 0.5558 0.100 Uiso 1 1 calc R . .
H14C H 0.2950 -0.1120 0.6379 0.100 Uiso 1 1 calc R . .
Cl1 Cl 0.06606(7) 0.25254(18) 0.45593(6) 0.0837(4) Uani 1 1 d . . .
Cl2 Cl 0.09044(8) 0.5162(2) 0.71586(7) 0.0954(5) Uani 1 1 d . . .
N1 N 0.2238(2) 0.4251(4) 0.68011(18) 0.0635(10) Uani 1 1 d . . .
O1 O 0.28384(18) 0.5850(4) 0.62348(16) 0.0737(9) Uani 1 1 d . . .
O2 O 0.18554(18) 0.0809(4) 0.63741(17) 0.0734(9) Uani 1 1 d . . .
O3 O 0.27278(17) 0.1008(4) 0.58860(16) 0.0690(8) Uani 1 1 d . . .
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 123.3(4) . . ?
C2 C1 Cl1 117.6(4) . . ?
C6 C1 Cl1 119.1(3) . . ?
C1 C2 C3 118.0(5) . . ?
C4 C3 C2 121.3(4) . . ?
C5 C4 C3 119.4(4) . . ?
C4 C5 C6 122.1(4) . . ?
C4 C5 Cl2 118.2(3) . . ?
C6 C5 Cl2 119.6(4) . . ?
C1 C6 C5 115.7(4) . . ?
C1 C6 C7 121.1(4) . . ?
C5 C6 C7 123.3(4) . . ?
C6 C7 N1 115.9(4) . . ?
C6 C7 C8 121.5(4) . . ?
N1 C7 C8 59.9(3) . . ?
C13 C8 N1 117.5(4) . . ?
C13 C8 C7 120.8(4) . . ?
N1 C8 C7 58.9(3) . . ?
C13 C8 C9 120.8(4) . . ?
N1 C8 C9 103.9(4) . . ?
C7 C8 C9 116.3(4) . . ?
O1 C9 C10 101.5(4) . . ?
O1 C9 C8 100.9(3) . . ?
C10 C9 C8 104.0(4) . . ?
C11 C10 C9 105.5(4) . . ?
C10 C11 C12 105.0(5) . . ?
O1 C12 C11 101.6(4) . . ?
O1 C12 N1 104.3(3) . . ?
C11 C12 N1 105.6(4) . . ?
O2 C13 O3 122.8(5) . . ?
O2 C13 C8 127.4(4) . . ?
O3 C13 C8 109.8(4) . . ?
C7 N1 C8 61.1(3) . . ?
C7 N1 C12 112.9(3) . . ?
C8 N1 C12 100.1(3) . . ?
C9 O1 C12 94.4(3) . . ?
C13 O3 C14 114.8(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.373(6) . ?
C1 C6 1.412(6) . ?
C1 Cl1 1.757(4) . ?
C2 C3 1.398(6) . ?
C3 C4 1.383(7) . ?
C4 C5 1.371(6) . ?
C5 C6 1.416(5) . ?
C5 Cl2 1.747(5) . ?
C6 C7 1.475(6) . ?
C7 N1 1.483(6) . ?
C7 C8 1.515(6) . ?
C8 C13 1.467(6) . ?
C8 N1 1.498(5) . ?
C8 C9 1.534(6) . ?
C9 O1 1.425(5) . ?
C9 C10 1.529(7) . ?
C10 C11 1.337(6) . ?
C11 C12 1.497(7) . ?
C12 O1 1.478(5) . ?
C12 N1 1.499(5) . ?
C13 O2 1.213(5) . ?
C13 O3 1.365(5) . ?
C14 O3 1.438(5) . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.0(8) . . . . ?
Cl1 C1 C2 C3 -180.0(4) . . . . ?
C1 C2 C3 C4 1.9(8) . . . . ?
C2 C3 C4 C5 -0.8(8) . . . . ?
C3 C4 C5 C6 -3.2(7) . . . . ?
C3 C4 C5 Cl2 173.8(4) . . . . ?
C2 C1 C6 C5 -4.6(7) . . . . ?
Cl1 C1 C6 C5 176.3(3) . . . . ?
C2 C1 C6 C7 175.0(5) . . . . ?
Cl1 C1 C6 C7 -4.1(6) . . . . ?
C4 C5 C6 C1 5.7(7) . . . . ?
Cl2 C5 C6 C1 -171.3(3) . . . . ?
C4 C5 C6 C7 -173.9(5) . . . . ?
Cl2 C5 C6 C7 9.1(6) . . . . ?
C1 C6 C7 N1 -135.5(4) . . . . ?
C5 C6 C7 N1 44.1(6) . . . . ?
C1 C6 C7 C8 -66.3(6) . . . . ?
C5 C6 C7 C8 113.3(5) . . . . ?
C6 C7 C8 C13 1.8(6) . . . . ?
N1 C7 C8 C13 105.6(4) . . . . ?
C6 C7 C8 N1 -103.8(4) . . . . ?
C6 C7 C8 C9 165.3(4) . . . . ?
N1 C7 C8 C9 -90.9(4) . . . . ?
C13 C8 C9 O1 -172.0(3) . . . . ?
N1 C8 C9 O1 -37.4(4) . . . . ?
C7 C8 C9 O1 24.5(4) . . . . ?
C13 C8 C9 C10 -67.0(5) . . . . ?
N1 C8 C9 C10 67.5(4) . . . . ?
C7 C8 C9 C10 129.5(4) . . . . ?
O1 C9 C10 C11 33.3(4) . . . . ?
C8 C9 C10 C11 -71.1(5) . . . . ?
C9 C10 C11 C12 1.2(5) . . . . ?
C10 C11 C12 O1 -34.1(5) . . . . ?
C10 C11 C12 N1 74.5(4) . . . . ?
N1 C8 C13 O2 35.0(6) . . . . ?
C7 C8 C13 O2 -33.4(6) . . . . ?
C9 C8 C13 O2 163.8(4) . . . . ?
N1 C8 C13 O3 -146.1(3) . . . . ?
C7 C8 C13 O3 145.4(3) . . . . ?
C9 C8 C13 O3 -17.4(5) . . . . ?
C6 C7 N1 C8 112.9(4) . . . . ?
C6 C7 N1 C12 -158.0(4) . . . . ?
C8 C7 N1 C12 89.1(4) . . . . ?
C13 C8 N1 C7 -111.1(4) . . . . ?
C9 C8 N1 C7 112.6(4) . . . . ?
C13 C8 N1 C12 138.2(4) . . . . ?
C7 C8 N1 C12 -110.7(4) . . . . ?
C9 C8 N1 C12 1.9(4) . . . . ?
O1 C12 N1 C7 -29.6(4) . . . . ?
C11 C12 N1 C7 -136.2(3) . . . . ?
O1 C12 N1 C8 33.2(4) . . . . ?
C11 C12 N1 C8 -73.5(4) . . . . ?
C10 C9 O1 C12 -51.3(4) . . . . ?
C8 C9 O1 C12 55.6(4) . . . . ?
C11 C12 O1 C9 52.7(4) . . . . ?
N1 C12 O1 C9 -56.9(4) . . . . ?
O2 C13 O3 C14 -2.1(6) . . . . ?
C8 C13 O3 C14 179.0(3) . . . . ?
