#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:25:53 +0100 (vie 25 de mar de 2016) $
#$Revision: 180078 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/24/7052469.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_7052469
loop_
_publ_author_name
'Eastmond, Geoffrey C.'
'Paprotny, Jerzy'
'Steiner, Alexander'
'Swanson, Linda'
_publ_section_title
;
 Synthesis of cyanodibenzo[1,4]dioxines and their derivatives by
 cyano-activated fluoro displacement reactions
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              379
_journal_paper_doi               10.1039/b008508l
_journal_volume                  25
_journal_year                    2001
_chemical_formula_sum            'C13 H7 N O2'
_chemical_formula_weight         209.20
_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                 106.80(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   27.732(6)
_cell_length_b                   7.833(2)
_cell_length_c                   19.416(4)
_cell_measurement_temperature    293(2)
_cell_volume                     4037.6(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.446
_diffrn_measured_fraction_theta_max 0.446
_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  0.1355
_diffrn_reflns_av_sigmaI/netI    0.1341
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10366
_diffrn_reflns_theta_full        22.46
_diffrn_reflns_theta_max         22.46
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.094
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.661
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     216
_refine_ls_restrained_S_all      0.636
_refine_ls_R_factor_all          0.1394
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0415P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                817
_reflns_number_total             2555
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b008508l.txt
_cod_data_source_block           geo7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0415P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0415P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        4037.6(16)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7052469
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.05491(10) 0.8974(5) 0.08429(17) 0.0889(11) Uani 1 d U . .
O2 O 0.16069(9) 0.8776(4) 0.14575(15) 0.0710(9) Uani 1 d U . .
N1 N 0.26227(15) 0.7084(7) 0.0994(2) 0.1164(18) Uani 1 d U . .
C1 C 0.2202(2) 0.7184(7) 0.0746(3) 0.0840(16) Uani 1 d U . .
C2 C 0.16572(16) 0.7314(6) 0.0418(2) 0.0663(13) Uani 1 d U . .
C3 C 0.14421(18) 0.6609(7) -0.0259(2) 0.0793(15) Uani 1 d U . .
H3 H 0.1640 0.6076 -0.0508 0.095 Uiso 1 calc R . .
C4 C 0.0925(2) 0.6721(7) -0.0552(3) 0.0884(16) Uani 1 d U . .
H4 H 0.0772 0.6269 -0.1005 0.106 Uiso 1 calc R . .
C5 C 0.06372(17) 0.7500(7) -0.0172(3) 0.0837(17) Uani 1 d U . .
H5 H 0.0290 0.7552 -0.0371 0.100 Uiso 1 calc R . .
C6 C 0.08507(15) 0.8196(6) 0.0488(2) 0.0674(13) Uani 1 d U . .
C7 C 0.13744(15) 0.8107(6) 0.0797(2) 0.0603(13) Uani 1 d U . .
C8 C 0.07819(16) 0.9630(7) 0.1517(3) 0.0715(14) Uani 1 d U . .
C9 C 0.04884(17) 1.0379(7) 0.1873(3) 0.0827(16) Uani 1 d U . .
H9 H 0.0141 1.0426 0.1667 0.099 Uiso 1 calc R . .
C10 C 0.07016(17) 1.1077(7) 0.2543(3) 0.0913(17) Uani 1 d U . .
H10 H 0.0499 1.1592 0.2791 0.110 Uiso 1 calc R . .
C11 C 0.12217(18) 1.1007(7) 0.2847(2) 0.0840(15) Uani 1 d U . .
H11 H 0.1369 1.1479 0.3299 0.101 Uiso 1 calc R . .
C12 C 0.15162(16) 1.0238(6) 0.2478(2) 0.0653(13) Uani 1 d U . .
H12 H 0.1863 1.0175 0.2681 0.078 Uiso 1 calc R . .
C13 C 0.12990(15) 0.9570(6) 0.1814(2) 0.0618(13) Uani 1 d U . .
O1' O 0.19509(11) 0.3396(5) 0.1502(2) 0.0995(12) Uani 1 d U . .
O2' O 0.08940(10) 0.3814(4) 0.09883(16) 0.0790(10) Uani 1 d U . .
N1' N -0.00452(16) 0.5677(7) 0.1604(2) 0.130(2) Uani 1 d U . .
C1' C 0.0373(2) 0.5486(7) 0.1795(3) 0.0886(16) Uani 1 d U . .
C2' C 0.09251(17) 0.5276(6) 0.2058(3) 0.0716(15) Uani 1 d U . .
C3' C 0.11740(18) 0.5903(7) 0.2737(2) 0.0833(15) Uani 1 d U . .
H3' H 0.0997 0.6447 0.3014 0.100 Uiso 1 calc R . .
C4' C 0.1687(2) 0.5702(8) 0.2990(3) 0.1003(18) Uani 1 d U . .
H4' H 0.1863 0.6114 0.3443 0.120 Uiso 1 calc R . .
C5' C 0.19407(19) 0.4882(8) 0.2566(3) 0.098(2) Uani 1 d U . .
H5' H 0.2289 0.4760 0.2737 0.117 Uiso 1 calc R . .
C6' C 0.16903(18) 0.4246(7) 0.1901(3) 0.0812(16) Uani 1 d U . .
C7' C 0.11650(17) 0.4442(7) 0.1640(3) 0.0698(14) Uani 1 d U . .
C8' C 0.1681(2) 0.2833(7) 0.0829(3) 0.0815(16) Uani 1 d U . .
C9' C 0.1933(2) 0.2037(8) 0.0413(3) 0.0968(19) Uani 1 d U . .
H9' H 0.2279 0.1882 0.0584 0.116 Uiso 1 calc R . .
C10' C 0.1673(3) 0.1463(8) -0.0260(4) 0.1057(19) Uani 1 d U . .
H10' H 0.1846 0.0943 -0.0548 0.127 Uiso 1 calc R . .
C11' C 0.1153(2) 0.1653(8) -0.0515(3) 0.0991(17) Uani 1 d U . .
H11' H 0.0976 0.1251 -0.0968 0.119 Uiso 1 calc R . .
C12' C 0.09053(19) 0.2452(7) -0.0081(3) 0.0830(16) Uani 1 d U . .
H12' H 0.0558 0.2601 -0.0246 0.100 Uiso 1 calc R . .
C13' C 0.11639(19) 0.3022(7) 0.0584(3) 0.0721(14) Uani 1 d U . .
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'
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
C6 O1 C8 117.1(3) . . ?
C7 O2 C13 116.6(3) . . ?
N1 C1 C2 179.6(6) . . ?
C7 C2 C3 122.1(4) . . ?
C7 C2 C1 118.5(4) . . ?
C3 C2 C1 119.3(5) . . ?
C4 C3 C2 118.3(5) . . ?
C5 C4 C3 120.0(5) . . ?
C6 C5 C4 121.4(5) . . ?
C5 C6 O1 119.3(4) . . ?
C5 C6 C7 119.9(5) . . ?
O1 C6 C7 120.9(4) . . ?
O2 C7 C2 119.4(4) . . ?
O2 C7 C6 122.2(4) . . ?
C2 C7 C6 118.3(4) . . ?
C9 C8 O1 117.6(4) . . ?
C9 C8 C13 120.5(5) . . ?
O1 C8 C13 121.9(5) . . ?
C8 C9 C10 120.0(5) . . ?
C9 C10 C11 119.7(5) . . ?
C12 C11 C10 119.7(5) . . ?
C13 C12 C11 119.8(4) . . ?
C12 C13 C8 120.3(5) . . ?
C12 C13 O2 118.4(4) . . ?
C8 C13 O2 121.2(4) . . ?
C6' O1' C8' 117.4(4) . . ?
C7' O2' C13' 116.5(4) . . ?
N1' C1' C2' 178.5(6) . . ?
C7' C2' C3' 122.9(5) . . ?
C7' C2' C1' 119.0(5) . . ?
C3' C2' C1' 118.0(5) . . ?
C4' C3' C2' 118.6(5) . . ?
C3' C4' C5' 119.4(5) . . ?
C6' C5' C4' 121.5(5) . . ?
C5' C6' O1' 120.1(5) . . ?
C5' C6' C7' 119.4(6) . . ?
O1' C6' C7' 120.5(5) . . ?
C2' C7' O2' 119.7(4) . . ?
C2' C7' C6' 118.2(5) . . ?
O2' C7' C6' 122.1(5) . . ?
C9' C8' O1' 118.6(5) . . ?
C9' C8' C13' 120.3(5) . . ?
O1' C8' C13' 121.1(5) . . ?
C8' C9' C10' 119.8(6) . . ?
C9' C10' C11' 120.6(6) . . ?
C12' C11' C10' 118.6(6) . . ?
C13' C12' C11' 120.6(5) . . ?
C12' C13' O2' 117.7(5) . . ?
C12' C13' C8' 120.1(5) . . ?
O2' C13' C8' 122.2(5) . . ?
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
O1 C6 1.371(5) . ?
O1 C8 1.380(5) . ?
O2 C7 1.362(4) . ?
O2 C13 1.392(5) . ?
N1 C1 1.128(5) . ?
C1 C2 1.464(6) . ?
C2 C7 1.370(6) . ?
C2 C3 1.391(6) . ?
C3 C4 1.385(5) . ?
C4 C5 1.375(6) . ?
C5 C6 1.361(6) . ?
C6 C7 1.404(5) . ?
C8 C9 1.346(6) . ?
C8 C13 1.383(5) . ?
C9 C10 1.376(6) . ?
C10 C11 1.393(5) . ?
C11 C12 1.372(6) . ?
C12 C13 1.360(5) . ?
O1' C6' 1.374(6) . ?
O1' C8' 1.378(5) . ?
O2' C7' 1.362(5) . ?
O2' C13' 1.379(5) . ?
N1' C1' 1.122(5) . ?
C1' C2' 1.476(7) . ?
C2' C7' 1.358(6) . ?
C2' C3' 1.389(6) . ?
C3' C4' 1.374(6) . ?
C4' C5' 1.385(7) . ?
C5' C6' 1.372(7) . ?
C6' C7' 1.406(6) . ?
C8' C9' 1.361(6) . ?
C8' C13' 1.382(6) . ?
C9' C10' 1.373(7) . ?
C10' C11' 1.390(6) . ?
C11' C12' 1.381(7) . ?
C12' C13' 1.359(6) . ?
