#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/40/7204028.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_7204028
loop_
_publ_author_name
'Scott, Janet L.'
'Raston, Colin L.'
_publ_section_title
;
 Solvent-free synthesis of 3-carboxycoumarins
;
_journal_issue                   5
_journal_name_full               'Green Chemistry'
_journal_page_first              245
_journal_paper_doi               10.1039/b006704k
_journal_volume                  2
_journal_year                    2000
_chemical_formula_moiety         'C14 H14 O6'
_chemical_formula_sum            'C14 H14 O6'
_chemical_formula_weight         278.25
_chemical_name_systematic        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.666(3)
_cell_angle_beta                 96.329(3)
_cell_angle_gamma                95.837(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9637(2)
_cell_length_b                   9.1230(6)
_cell_length_c                   12.0646(7)
_cell_measurement_temperature    123(2)
_cell_volume                     638.28(6)
_computing_molecular_graphics    'ORTEP-3 for Windows v 1.05'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Enraf Nonius Kappa CCD'
_diffrn_measurement_method       '1 degree, phi and omega scans'
_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    0.0539
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2985
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         3.46
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_correction_T_min  0.9557
_exptl_crystal_colour            'bright yellow'
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2985
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0437
_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)+(0.0396P)²+0.2134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1038
_reflns_number_gt                2221
_reflns_number_total             2985
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b006704k.txt
_cod_data_source_block           compound3a
_cod_original_sg_symbol_H-M      P1(bar)
_cod_database_code               7204028
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O3 O 0.05678(17) 0.27752(12) 0.24409(9) 0.0213(3) Uani 1 1 d . . .
O1 O -0.20734(17) -0.15471(12) -0.04524(9) 0.0203(3) Uani 1 1 d D . .
O2 O -0.50505(18) -0.38230(12) -0.15704(9) 0.0227(3) Uani 1 1 d . . .
O6 O -0.29233(18) -0.13961(12) 0.35860(9) 0.0222(3) Uani 1 1 d . . .
O4 O -0.07286(17) 0.29472(12) 0.40866(8) 0.0186(2) Uani 1 1 d . . .
O5 O -0.24906(17) 0.08355(12) 0.46788(8) 0.0184(2) Uani 1 1 d . . .
C2 C -0.3954(2) -0.19420(16) 0.00128(12) 0.0150(3) Uani 1 1 d . . .
C1 C -0.4262(2) -0.11456(16) 0.10688(12) 0.0156(3) Uani 1 1 d . . .
C3 C -0.5575(2) -0.31477(16) -0.05466(12) 0.0166(3) Uani 1 1 d . . .
C4 C -0.7497(3) -0.35206(18) -0.00656(13) 0.0210(3) Uani 1 1 d . . .
H4 H -0.8581 -0.4339 -0.0438 0.025 Uiso 1 1 calc R . .
C10 C -0.0643(2) 0.21957(17) 0.30289(12) 0.0160(3) Uani 1 1 d . . .
C7 C -0.2596(2) 0.01339(17) 0.15931(12) 0.0160(3) Uani 1 1 d . . .
H7 H -0.1802 0.0618 0.1087 0.019 Uiso 1 1 calc R . .
C14 C -0.2588(2) -0.00590(17) 0.36520(12) 0.0168(3) Uani 1 1 d . . .
C6 C -0.6261(2) -0.15277(18) 0.15312(13) 0.0190(3) Uani 1 1 d . . .
H6 H -0.6517 -0.0976 0.2237 0.023 Uiso 1 1 calc R . .
C9 C -0.2038(2) 0.07175(16) 0.27066(12) 0.0157(3) Uani 1 1 d . . .
C11 C -0.2490(2) 0.24259(17) 0.47160(12) 0.0171(3) Uani 1 1 d . . .
C5 C -0.7847(3) -0.26902(18) 0.09714(13) 0.0214(3) Uani 1 1 d . . .
H5 H -0.9193 -0.2931 0.1292 0.026 Uiso 1 1 calc R . .
C8 C -0.6446(3) -0.51737(18) -0.21197(13) 0.0227(3) Uani 1 1 d . . .
H8A H -0.6419 -0.5912 -0.1617 0.034 Uiso 1 1 calc R . .
H8B H -0.5865 -0.5574 -0.2823 0.034 Uiso 1 1 calc R . .
H8C H -0.8011 -0.4961 -0.2296 0.034 Uiso 1 1 calc R . .
C12 C -0.1775(3) 0.31593(19) 0.59315(13) 0.0222(3) Uani 1 1 d . . .
H12A H -0.2914 0.2839 0.6397 0.033 Uiso 1 1 calc R . .
H12B H -0.1644 0.4250 0.5993 0.033 Uiso 1 1 calc R . .
H12C H -0.0302 0.2867 0.6197 0.033 Uiso 1 1 calc R . .
C13 C -0.4789(3) 0.27633(19) 0.42318(13) 0.0221(3) Uani 1 1 d . . .
H13A H -0.5122 0.2282 0.3432 0.033 Uiso 1 1 calc R . .
H13B H -0.4776 0.3849 0.4294 0.033 Uiso 1 1 calc R . .
H13C H -0.5958 0.2378 0.4655 0.033 Uiso 1 1 calc R . .
H1 H -0.201(4) -0.215(2) -0.1172(15) 0.053(6) Uiso 1 1 d 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'
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
C3 O2 C8 117.05(12) . . ?
C10 O4 C11 118.45(11) . . ?
C14 O5 C11 118.12(11) . . ?
O1 C2 C1 118.90(13) . . ?
O1 C2 C3 120.91(13) . . ?
C1 C2 C3 120.19(13) . . ?
C2 C1 C6 118.65(13) . . ?
C2 C1 C7 118.30(13) . . ?
C6 C1 C7 122.80(13) . . ?
O2 C3 C4 126.17(13) . . ?
O2 C3 C2 113.75(13) . . ?
C4 C3 C2 120.05(14) . . ?
C3 C4 C5 119.80(14) . . ?
O3 C10 O4 117.83(13) . . ?
O3 C10 C9 126.09(13) . . ?
O4 C10 C9 116.07(12) . . ?
C9 C7 C1 128.19(14) . . ?
O6 C14 O5 118.93(13) . . ?
O6 C14 C9 125.09(14) . . ?
O5 C14 C9 115.70(13) . . ?
C5 C6 C1 120.69(14) . . ?
C7 C9 C10 118.40(13) . . ?
C7 C9 C14 124.96(14) . . ?
C10 C9 C14 116.50(12) . . ?
O5 C11 O4 108.89(11) . . ?
O5 C11 C12 106.33(12) . . ?
O4 C11 C12 106.17(12) . . ?
O5 C11 C13 110.61(12) . . ?
O4 C11 C13 110.79(12) . . ?
C12 C11 C13 113.80(13) . . ?
C6 C5 C4 120.55(14) . . ?
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
O3 C10 1.2105(17) . ?
O1 C2 1.3519(17) . ?
O2 C3 1.3681(18) . ?
O2 C8 1.4304(18) . ?
O6 C14 1.2035(18) . ?
O4 C10 1.3522(17) . ?
O4 C11 1.4496(17) . ?
O5 C14 1.3561(18) . ?
O5 C11 1.4440(18) . ?
C2 C1 1.397(2) . ?
C2 C3 1.411(2) . ?
C1 C6 1.408(2) . ?
C1 C7 1.459(2) . ?
C3 C4 1.379(2) . ?
C4 C5 1.398(2) . ?
C10 C9 1.479(2) . ?
C7 C9 1.351(2) . ?
C14 C9 1.489(2) . ?
C6 C5 1.375(2) . ?
C11 C12 1.501(2) . ?
C11 C13 1.512(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653697
