#------------------------------------------------------------------------------
#$Date: 2018-03-15 18:33:54 +0200 (Thu, 15 Mar 2018) $
#$Revision: 206958 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/55/7105518.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_7105518
loop_
_publ_author_name
'Panda, Biswajit'
'Sarkar, Tarun K.'
_publ_section_title
;
 Gold and palladium combined for the Sonogashira-type cross-coupling of
 arenediazonium salts
;
_journal_issue                   18
_journal_name_full               'Chemical Communications'
_journal_page_first              3131
_journal_page_last               3133
_journal_paper_doi               10.1039/c001277g
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C14 H8 N2 O4'
_chemical_formula_weight         268.10
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 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                 95.245(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.0640(10)
_cell_length_b                   12.9928(10)
_cell_length_c                   14.0524(11)
_cell_measurement_temperature    293(2)
_cell_volume                     2375.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.897
_diffrn_measured_fraction_theta_max 0.897
_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  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17240
_diffrn_reflns_theta_full        31.73
_diffrn_reflns_theta_max         31.73
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0534P)²+1.2718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1463
_reflns_number_gt                1745
_reflns_number_total             3627
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c001277g.txt
_cod_data_source_block           tksbp715u_0m
_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 

2018-02-22
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C16 H9.14 N2.29 O4.57'
_cod_original_formula_weight         306.54
_cod_original_formula_units_Z            7
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               7105518
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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
C5 C 0.12892(13) 0.86580(13) 0.12086(11) 0.0440(4) Uani 1 1 d . . .
C4 C 0.13001(14) 0.76747(14) 0.16406(12) 0.0473(4) Uani 1 1 d . . .
H4 H 0.1360 0.7595 0.2301 0.057 Uiso 1 1 calc R . .
C6 C 0.12135(15) 0.87531(15) 0.01992(12) 0.0512(5) Uani 1 1 d . . .
O1 O 0.14251(13) 0.93620(11) 0.31360(9) 0.0735(5) Uani 1 1 d . . .
O2 O 0.12902(12) 1.02900(10) 0.07722(8) 0.0644(4) Uani 1 1 d . . .
C7 C 0.13239(14) 0.96575(14) 0.15317(12) 0.0488(5) Uani 1 1 d . . .
C8 C 0.13610(15) 1.00399(15) 0.25320(12) 0.0508(5) Uani 1 1 d . . .
N2 N 0.11981(14) 0.58243(13) 0.14631(13) 0.0655(5) Uani 1 1 d . . .
C1 C 0.11335(16) 0.78662(17) -0.03979(13) 0.0608(5) Uani 1 1 d . . .
H1 H 0.1083 0.7926 -0.1060 0.073 Uiso 1 1 calc R . .
C3 C 0.12186(14) 0.68592(14) 0.10453(13) 0.0498(5) Uani 1 1 d . . .
N1 N 0.12193(15) 0.97276(14) -0.00791(11) 0.0689(5) Uani 1 1 d . . .
C9 C 0.13157(14) 1.11410(14) 0.27893(13) 0.0496(5) Uani 1 1 d . . .
O3 O 0.12483(14) 0.57361(11) 0.23320(11) 0.0771(5) Uani 1 1 d . . .
C14 C 0.14607(16) 1.13907(17) 0.37579(14) 0.0628(6) Uani 1 1 d . . .
H14 H 0.1578 1.0873 0.4212 0.075 Uiso 1 1 calc R . .
C10 C 0.11295(16) 1.19370(15) 0.21309(15) 0.0593(5) Uani 1 1 d . . .
H10 H 0.1025 1.1787 0.1482 0.071 Uiso 1 1 calc R . .
C2 C 0.11336(16) 0.69383(16) 0.00278(13) 0.0586(5) Uani 1 1 d . . .
H2 H 0.1078 0.6345 -0.0343 0.070 Uiso 1 1 calc R . .
O4 O 0.11259(17) 0.50905(13) 0.09185(13) 0.1041(7) Uani 1 1 d . . .
C13 C 0.14300(17) 1.24078(19) 0.40431(17) 0.0736(7) Uani 1 1 d . . .
H13 H 0.1529 1.2569 0.4690 0.088 Uiso 1 1 calc R . .
C11 C 0.10988(17) 1.29453(17) 0.24340(18) 0.0702(6) Uani 1 1 d . . .
H11 H 0.0970 1.3469 0.1987 0.084 Uiso 1 1 calc R . .
C12 C 0.12553(16) 1.31840(19) 0.33841(19) 0.0744(7) Uani 1 1 d . . .
H12 H 0.1243 1.3866 0.3583 0.089 Uiso 1 1 calc R . .
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
C7 C5 C4 135.47(16) . . ?
C7 C5 C6 104.19(15) . . ?
C4 C5 C6 120.34(16) . . ?
C3 C4 C5 116.53(16) . . ?
N1 C6 C5 112.12(16) . . ?
N1 C6 C1 126.97(17) . . ?
C5 C6 C1 120.90(17) . . ?
C7 O2 N1 110.77(13) . . ?
O2 C7 C5 108.51(14) . . ?
O2 C7 C8 122.81(16) . . ?
C5 C7 C8 128.66(15) . . ?
O1 C8 C9 122.00(16) . . ?
O1 C8 C7 114.22(17) . . ?
C9 C8 C7 123.77(15) . . ?
O3 N2 O4 123.18(19) . . ?
O3 N2 C3 118.95(17) . . ?
O4 N2 C3 117.88(18) . . ?
C2 C1 C6 117.78(17) . . ?
C4 C3 C2 124.01(18) . . ?
C4 C3 N2 118.35(17) . . ?
C2 C3 N2 117.63(17) . . ?
C6 N1 O2 104.39(14) . . ?
C10 C9 C14 118.35(18) . . ?
C10 C9 C8 124.34(17) . . ?
C14 C9 C8 117.31(17) . . ?
C13 C14 C9 120.0(2) . . ?
C11 C10 C9 120.5(2) . . ?
C1 C2 C3 120.43(18) . . ?
C12 C13 C14 120.9(2) . . ?
C12 C11 C10 120.7(2) . . ?
C11 C12 C13 119.5(2) . . ?
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
C5 C7 1.375(2) . ?
C5 C4 1.414(2) . ?
C5 C6 1.418(2) . ?
C4 C3 1.348(2) . ?
C6 N1 1.325(2) . ?
C6 C1 1.424(3) . ?
O1 C8 1.221(2) . ?
O2 C7 1.345(2) . ?
O2 N1 1.3976(19) . ?
C7 C8 1.488(2) . ?
C8 C9 1.478(3) . ?
N2 O3 1.222(2) . ?
N2 O4 1.221(2) . ?
N2 C3 1.468(3) . ?
C1 C2 1.346(3) . ?
C3 C2 1.428(2) . ?
C9 C10 1.394(3) . ?
C9 C14 1.395(3) . ?
C14 C13 1.383(3) . ?
C10 C11 1.379(3) . ?
C13 C12 1.374(3) . ?
C11 C12 1.368(3) . ?
