#------------------------------------------------------------------------------
#$Date: 2025-08-22 13:33:34 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301861 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/00/7150009.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_7150009
loop_
_publ_author_name
'Pittelkow, Michael'
'Boas, Ulrik'
'Jessing, Mikkel'
'Jensen, Knud J.'
'Christensen, Jørn B'
_publ_section_title
;
 Role of the peri-effect in synthesis and reactivity of highly
 substituted naphthaldehydes: a novel backbone amide linker for
 solid-phase synthesis.
;
_journal_issue                   3
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              508
_journal_page_last               514
_journal_paper_doi               10.1039/b412971g
_journal_volume                  3
_journal_year                    2005
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C13 H12 O4 '
_chemical_formula_sum            'C13 H12 O4'
_chemical_formula_weight         232.235
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 103.443(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.985(3)
_cell_length_b                   3.9181(6)
_cell_length_c                   14.504(2)
_cell_measurement_temperature    122
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      1.10
_cell_volume                     1049.3(3)
_computing_cell_refinement       'COLLECT (Nonius. 1999)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'EvalCCD (Duisenberg, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (ALTOMARE, 1999)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            38108
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.10
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needles
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0529
_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)+ (0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.1729
_reflns_number_gt                2159
_reflns_number_total             3077
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b412971g-esi.txt
_cod_data_source_block           compound_2
_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_sg_symbol_H-M      'P 21/c        '
_cod_original_formula_sum        'C13 H12 O4 '
_cod_database_code               7150009
loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
-X,-Y,-Z
'-X,+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
O1 O 0.23490(5) -0.2771(3) 0.49990(7) 0.0210(3) Uani 1 1 d . . .
O2 O 0.06153(5) 0.1543(3) 0.09177(7) 0.0192(3) Uani 1 1 d . . .
O3 O 0.36472(6) -0.2504(3) 0.60069(8) 0.0282(3) Uani 1 1 d . . .
O4 O 0.42443(5) 0.2755(3) 0.39717(7) 0.0215(3) Uani 1 1 d . . .
C5 C 0.11303(7) 0.1012(4) 0.17281(10) 0.0151(3) Uani 1 1 d . . .
C6 C 0.23311(7) 0.1353(4) 0.27448(10) 0.0144(3) Uani 1 1 d . . .
C7 C 0.13518(8) -0.1443(4) 0.32870(10) 0.0165(3) Uani 1 1 d . . .
C8 C 0.18405(7) 0.2036(4) 0.18701(10) 0.0154(3) Uani 1 1 d . . .
C9 C 0.35347(7) 0.1785(4) 0.37446(10) 0.0171(3) Uani 1 1 d . . .
C10 C 0.08821(7) -0.0742(4) 0.24398(10) 0.0169(3) Uani 1 1 d . . .
C11 C 0.33093(7) -0.0029(4) 0.44832(10) 0.0169(3) Uani 1 1 d . . .
C12 C 0.30659(8) 0.2439(4) 0.28986(10) 0.0165(3) Uani 1 1 d . . .
C13 C 0.08405(8) 0.3187(4) 0.01540(10) 0.0195(3) Uani 1 1 d . . .
C14 C 0.25863(7) -0.1081(4) 0.43266(10) 0.0158(3) Uani 1 1 d . . .
C15 C 0.38125(8) -0.0909(5) 0.53500(11) 0.0232(4) Uani 1 1 d . . .
C16 C 0.45085(8) 0.4420(4) 0.32463(11) 0.0239(4) Uani 1 1 d . . .
C17 C 0.20834(7) -0.0394(4) 0.34611(10) 0.0148(3) Uani 1 1 d . . .
H1 H 0.2730 -0.3107 0.5502 0.025 Uiso 1 1 d R . .
H7 H 0.1193 -0.2754 0.3776 0.020 Uiso 1 1 d R . .
H8 H 0.2028 0.3172 0.1386 0.019 Uiso 1 1 d R . .
H10 H 0.0385 -0.1403 0.2318 0.020 Uiso 1 1 d R . .
H12 H 0.3224 0.3719 0.2424 0.020 Uiso 1 1 d R . .
H13A H 0.1189 0.2072 0.0023 0.023 Uiso 1 1 d R . .
H13B H 0.1019 0.5445 0.0300 0.023 Uiso 1 1 d R . .
H13C H 0.0440 0.3203 -0.0382 0.023 Uiso 1 1 d R . .
H15 H 0.4314 -0.0033 0.5425 0.028 Uiso 1 1 d R . .
H16A H 0.4445 0.3003 0.2696 0.029 Uiso 1 1 d R . .
H16B H 0.4330 0.6366 0.3085 0.029 Uiso 1 1 d R . .
H16C H 0.5018 0.4781 0.3501 0.029 Uiso 1 1 d 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_radiation_wavelength
0.71073
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
C5 O2 C13 117.04(11) . . ?
C9 O4 C16 116.53(11) . . ?
O2 C5 C8 124.60(13) . . ?
O2 C5 C10 114.36(12) . . ?
C8 C5 C10 121.04(13) . . ?
C17 C6 C8 119.28(12) . . ?
C17 C6 C12 120.70(12) . . ?
C8 C6 C12 120.02(13) . . ?
C10 C7 C17 120.68(13) . . ?
C5 C8 C6 119.82(13) . . ?
C12 C9 O4 124.52(14) . . ?
C12 C9 C11 121.41(13) . . ?
O4 C9 C11 114.07(12) . . ?
C7 C10 C5 119.79(13) . . ?
C14 C11 C9 118.49(12) . . ?
C14 C11 C15 120.01(13) . . ?
C9 C11 C15 121.44(13) . . ?
C9 C12 C6 119.70(14) . . ?
O1 C14 C11 120.66(12) . . ?
O1 C14 C17 117.90(12) . . ?
C11 C14 C17 121.45(13) . . ?
O3 C15 C11 124.01(14) . . ?
C6 C17 C7 119.39(12) . . ?
C6 C17 C14 118.24(12) . . ?
C7 C17 C14 122.36(13) . . ?
C14 O1 H1 108.4 . . ?
C10 C7 H7 120.7 . . ?
C17 C7 H7 118.6 . . ?
C5 C8 H8 122.6 . . ?
C6 C8 H8 117.6 . . ?
C7 C10 H10 121.5 . . ?
C5 C10 H10 118.8 . . ?
C9 C12 H12 120.0 . . ?
C6 C12 H12 120.2 . . ?
O2 C13 H13A 109.3 . . ?
O2 C13 H13B 113.7 . . ?
H13A C13 H13B 105.7 . . ?
O2 C13 H13C 108.1 . . ?
H13A C13 H13C 109.6 . . ?
H13B C13 H13C 110.5 . . ?
O3 C15 H15 119.9 . . ?
C11 C15 H15 116.0 . . ?
O4 C16 H16A 110.7 . . ?
O4 C16 H16B 115.5 . . ?
H16A C16 H16B 109.1 . . ?
O4 C16 H16C 106.2 . . ?
H16A C16 H16C 109.0 . . ?
H16B C16 H16C 106.0 . . ?
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 C14 1.3405(17) . ?
O2 C5 1.3588(16) . ?
O2 C13 1.4299(17) . ?
O3 C15 1.2394(19) . ?
O4 C9 1.3645(16) . ?
O4 C16 1.4244(18) . ?
C5 C8 1.3758(19) . ?
C5 C10 1.409(2) . ?
C6 C17 1.413(2) . ?
C6 C8 1.4139(19) . ?
C6 C12 1.4255(19) . ?
C7 C10 1.368(2) . ?
C7 C17 1.4137(19) . ?
C9 C12 1.362(2) . ?
C9 C11 1.431(2) . ?
C11 C14 1.4003(19) . ?
C11 C15 1.4329(19) . ?
C14 C17 1.4151(19) . ?
O1 H1 0.9093 . ?
C7 H7 0.9775 . ?
C8 H8 0.9659 . ?
C10 H10 0.9538 . ?
C12 H12 0.9551 . ?
C13 H13A 0.8508 . ?
C13 H13B 0.9538 . ?
C13 H13C 0.9525 . ?
C15 H15 0.9943 . ?
C16 H16A 0.9572 . ?
C16 H16B 0.8455 . ?
C16 H16C 0.9617 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9656489
2 PubChem 11481669
