#------------------------------------------------------------------------------
#$Date: 2025-08-22 13:33:34 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301861 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/00/7150008.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_7150008
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         'C14 H14 O4 '
_chemical_formula_sum            'C14 H14 O4'
_chemical_formula_weight         246.262
_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                 94.353(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.9763(3)
_cell_length_b                   11.8245(10)
_cell_length_c                   24.323(2)
_cell_measurement_reflns_used    10359
_cell_measurement_temperature    122
_cell_measurement_theta_max      31.98
_cell_measurement_theta_min      1.68
_cell_volume                     1140.31(16)
_computing_cell_refinement       'COLLECT (Nonius, 1999)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'EvalCCD(Duisberg, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_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       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            30841
_diffrn_reflns_theta_full        31.98
_diffrn_reflns_theta_max         31.98
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needles
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.255
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.255
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.001
_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          0.1606
_refine_ls_wR_factor_ref         0.1900
_reflns_number_gt                2620
_reflns_number_total             3800
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b412971g-esi.txt
_cod_data_source_block           compound_1
_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        1139.2(2)
_cod_original_sg_symbol_H-M      'P 21/c        '
_cod_original_formula_sum        'C14 H14 O4 '
_cod_database_code               7150008
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 0.9889(3) 0.27485(9) 0.82596(4) 0.0197(3) Uani 1 1 d . . .
O2 O 0.3792(3) 0.01267(9) 0.56449(4) 0.0180(3) Uani 1 1 d . . .
O3 O 0.1800(3) 0.40078(9) 0.60043(4) 0.0171(3) Uani 1 1 d . . .
C4 C 0.6417(4) 0.18727(12) 0.68648(6) 0.0128(3) Uani 1 1 d . . .
O5 O -0.0558(3) 0.28229(10) 0.50325(5) 0.0249(3) Uani 1 1 d . . .
C6 C 0.6070(4) 0.09187(12) 0.65128(6) 0.0139(3) Uani 1 1 d . . .
C7 C 0.8397(4) 0.27290(13) 0.77344(6) 0.0153(3) Uani 1 1 d . . .
C8 C 0.4266(4) 0.09992(13) 0.60089(6) 0.0139(3) Uani 1 1 d . . .
C9 C 0.3205(4) 0.29867(13) 0.61535(6) 0.0143(3) Uani 1 1 d . . .
C10 C 0.5371(4) 0.38651(13) 0.70386(6) 0.0159(3) Uani 1 1 d . . .
C11 C 0.8132(4) 0.17932(13) 0.73999(6) 0.0145(3) Uani 1 1 d . . .
C12 C 0.4988(4) 0.29186(12) 0.66834(6) 0.0134(3) Uani 1 1 d . . .
C13 C 0.2744(4) 0.20403(12) 0.58177(6) 0.0137(3) Uani 1 1 d . . .
C14 C 1.1320(4) 0.17273(13) 0.84818(6) 0.0210(4) Uani 1 1 d . . .
C15 C 0.3581(4) 0.46303(13) 0.56119(6) 0.0206(3) Uani 1 1 d . . .
C16 C 0.0515(4) 0.20211(13) 0.53007(6) 0.0178(3) Uani 1 1 d . . .
C17 C 0.7022(4) 0.37733(13) 0.75498(6) 0.0172(3) Uani 1 1 d . . .
C18 C 0.5300(4) -0.09312(12) 0.58076(6) 0.0185(3) Uani 1 1 d . . .
H6 H 0.7354 0.0217 0.6623 0.017 Uiso 1 1 d R . .
H10 H 0.4235 0.4533 0.6923 0.019 Uiso 1 1 d R . .
H11 H 0.9057 0.1068 0.7528 0.017 Uiso 1 1 d R . .
H14A H 1.2847 0.1466 0.8306 0.025 Uiso 1 1 d R . .
H14B H 1.1935 0.1862 0.8860 0.025 Uiso 1 1 d R . .
H14C H 0.9728 0.1111 0.8473 0.025 Uiso 1 1 d R . .
H15A H 0.2211 0.5254 0.5517 0.025 Uiso 1 1 d R . .
H15B H 0.5572 0.4800 0.5752 0.025 Uiso 1 1 d R . .
H15C H 0.3765 0.4265 0.5362 0.025 Uiso 1 1 d R . .
H16 H -0.0013 0.1386 0.5198 0.021 Uiso 1 1 d R . .
H17 H 0.7410 0.4390 0.7784 0.021 Uiso 1 1 d R . .
H18A H 0.4616 -0.1169 0.6106 0.022 Uiso 1 1 d R . .
H18B H 0.4601 -0.1432 0.5517 0.022 Uiso 1 1 d R . .
H18C H 0.7873 -0.0848 0.5879 0.022 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
C7 O1 C14 118.02(12) . . ?
C8 O2 C18 116.91(11) . . ?
C9 O3 C15 114.49(11) . . ?
C12 C4 C6 119.51(13) . . ?
C12 C4 C11 119.44(13) . . ?
C6 C4 C11 121.05(13) . . ?
C8 C6 C4 120.15(13) . . ?
O1 C7 C11 125.09(13) . . ?
O1 C7 C17 114.19(13) . . ?
C11 C7 C17 120.71(13) . . ?
O2 C8 C6 124.17(13) . . ?
O2 C8 C13 114.21(12) . . ?
C6 C8 C13 121.62(13) . . ?
O3 C9 C13 121.77(13) . . ?
O3 C9 C12 116.87(13) . . ?
C13 C9 C12 121.25(13) . . ?
C17 C10 C12 120.89(14) . . ?
C7 C11 C4 119.76(13) . . ?
C4 C12 C10 118.85(13) . . ?
C4 C12 C9 119.21(13) . . ?
C10 C12 C9 121.94(13) . . ?
C9 C13 C8 118.18(13) . . ?
C9 C13 C16 123.56(13) . . ?
C8 C13 C16 117.99(13) . . ?
O5 C16 C13 127.33(15) . . ?
C10 C17 C7 120.33(14) . . ?
C8 C6 H6 121.0 . . ?
C4 C6 H6 118.6 . . ?
C17 C10 H10 121.5 . . ?
C12 C10 H10 117.3 . . ?
C7 C11 H11 120.8 . . ?
C4 C11 H11 119.4 . . ?
O1 C14 H14A 113.9 . . ?
O1 C14 H14B 106.7 . . ?
H14A C14 H14B 115.2 . . ?
O1 C14 H14C 113.2 . . ?
H14A C14 H14C 102.4 . . ?
H14B C14 H14C 105.1 . . ?
O3 C15 H15A 104.9 . . ?
O3 C15 H15B 110.3 . . ?
H15A C15 H15B 114.3 . . ?
O3 C15 H15C 109.2 . . ?
H15A C15 H15C 110.3 . . ?
H15B C15 H15C 107.6 . . ?
O5 C16 H16 119.3 . . ?
C13 C16 H16 113.3 . . ?
C10 C17 H17 122.6 . . ?
C7 C17 H17 116.9 . . ?
O2 C18 H18A 111.7 . . ?
O2 C18 H18B 104.6 . . ?
H18A C18 H18B 109.8 . . ?
O2 C18 H18C 110.5 . . ?
H18A C18 H18C 106.1 . . ?
H18B C18 H18C 114.2 . . ?
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
O1 C7 1.3607(17) . ?
O1 C14 1.4212(18) . ?
O2 C8 1.3617(17) . ?
O2 C18 1.4281(17) . ?
O3 C9 1.3661(17) . ?
O3 C15 1.4398(18) . ?
C4 C12 1.4153(19) . ?
C4 C6 1.416(2) . ?
C4 C11 1.4184(19) . ?
O5 C16 1.2073(18) . ?
C6 C8 1.3680(19) . ?
C7 C11 1.372(2) . ?
C7 C17 1.408(2) . ?
C8 C13 1.431(2) . ?
C9 C13 1.388(2) . ?
C9 C12 1.418(2) . ?
C10 C17 1.358(2) . ?
C10 C12 1.414(2) . ?
C13 C16 1.4739(19) . ?
C6 H6 0.9990 . ?
C10 H10 0.9406 . ?
C11 H11 0.9734 . ?
C14 H14A 0.8323 . ?
C14 H14B 0.9449 . ?
C14 H14C 0.9641 . ?
C15 H15A 0.9337 . ?
C15 H15B 0.8573 . ?
C15 H15C 0.7552 . ?
C16 H16 0.8129 . ?
C17 H17 0.9308 . ?
C18 H18A 0.8445 . ?
C18 H18B 0.9453 . ?
C18 H18C 1.0271 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9588799
2 PubChem 11413912
