#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/33/4023318.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_4023318
loop_
_publ_author_name
'Andrew N. Lowell'
'Michael W. Fennie'
'Marisa C. Kozlowski'
_publ_section_title
;
 A Concise Synthesis of the Naphthalene Portion of Purpuromycin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1911
_journal_page_last               1918
_journal_paper_doi               10.1021/jo7024114
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C23 H24 O7'
_chemical_formula_weight         412.42
_chemical_melting_point          121.5(5)
_chemical_name_common
' Cpd 2: 3-(Benzyloxy)-1,4,5,6,8-pentamethoxynaphthalene-2-carbaldehyde '
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.162(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4788(14)
_cell_length_b                   19.010(3)
_cell_length_c                   12.1060(19)
_cell_measurement_temperature    143(1)
_cell_volume                     2020.3(5)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0895
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9716
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7701
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.828
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.828
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0418
_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)+(0.0344P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                1789
_reflns_number_total             3543
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7024114-File001.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '121-122' was changed to '121.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n     '
_cod_database_code               4023318
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7581(2) 0.42997(12) 0.1769(2) 0.0285(5) Uani 1 1 d . . .
C2 C 0.8658(2) 0.47724(12) 0.24646(19) 0.0266(5) Uani 1 1 d . . .
C3 C 0.8345(2) 0.52647(11) 0.32255(18) 0.0236(5) Uani 1 1 d . . .
C4 C 0.9466(2) 0.57154(12) 0.40402(19) 0.0262(5) Uani 1 1 d . . .
C5 C 0.9093(2) 0.61802(11) 0.47526(19) 0.0278(6) Uani 1 1 d . . .
H5 H 0.9845 0.6458 0.5296 0.037 Uiso 1 1 calc R . .
C6 C 0.7582(2) 0.62374(12) 0.46628(19) 0.0266(5) Uani 1 1 d . . .
C7 C 0.6454(2) 0.58261(12) 0.38795(19) 0.0255(5) Uani 1 1 d . . .
C8 C 0.6803(2) 0.53144(11) 0.31748(18) 0.0227(5) Uani 1 1 d . . .
C9 C 0.5703(2) 0.48248(11) 0.24346(19) 0.0245(5) Uani 1 1 d . . .
C10 C 0.6093(2) 0.43231(12) 0.17952(19) 0.0266(5) Uani 1 1 d . . .
C11 C 0.8018(3) 0.38032(14) 0.1024(2) 0.0444(7) Uani 1 1 d . . .
H11 H 0.9040 0.3800 0.1124 0.059 Uiso 1 1 calc R . .
C12 C 1.0292(2) 0.52799(14) 0.1635(2) 0.0458(7) Uani 1 1 d . . .
H12A H 0.9570 0.5212 0.0836 0.069 Uiso 1 1 calc R . .
H12B H 1.1307 0.5249 0.1643 0.069 Uiso 1 1 calc R . .
H12C H 1.0141 0.5735 0.1915 0.069 Uiso 1 1 calc R . .
C13 C 1.2026(2) 0.61444(13) 0.4840(2) 0.0364(6) Uani 1 1 d . . .
H13A H 1.1693 0.6616 0.4595 0.055 Uiso 1 1 calc R . .
H13B H 1.2990 0.6065 0.4772 0.055 Uiso 1 1 calc R . .
H13C H 1.2132 0.6079 0.5654 0.055 Uiso 1 1 calc R . .
C14 C 0.8317(2) 0.70479(13) 0.6284(2) 0.0423(7) Uani 1 1 d . . .
H14A H 0.9000 0.6705 0.6790 0.063 Uiso 1 1 calc R . .
H14B H 0.7870 0.7317 0.6739 0.063 Uiso 1 1 calc R . .
H14C H 0.8870 0.7356 0.5963 0.063 Uiso 1 1 calc R . .
C15 C 0.4157(2) 0.64234(13) 0.2926(2) 0.0395(6) Uani 1 1 d . . .
H15A H 0.4690 0.6864 0.3079 0.059 Uiso 1 1 calc R . .
H15B H 0.3157 0.6490 0.2934 0.059 Uiso 1 1 calc R . .
H15C H 0.4074 0.6249 0.2160 0.059 Uiso 1 1 calc R . .
C16 C 0.3952(2) 0.44566(13) 0.3271(2) 0.0398(7) Uani 1 1 d . . .
H16A H 0.4119 0.3965 0.3185 0.060 Uiso 1 1 calc R . .
H16B H 0.2924 0.4528 0.3211 0.060 Uiso 1 1 calc R . .
H16C H 0.4645 0.4617 0.4035 0.060 Uiso 1 1 calc R . .
C17 C 0.4049(2) 0.40190(13) 0.0033(2) 0.0391(6) Uani 1 1 d . . .
H17A H 0.4629 0.4072 -0.0472 0.052 Uiso 1 1 calc R . .
H17B H 0.3573 0.4467 0.0063 0.052 Uiso 1 1 calc R . .
C18 C 0.2849(2) 0.34621(12) -0.0468(2) 0.0321(6) Uani 1 1 d . . .
C19 C 0.2653(2) 0.31372(13) -0.1534(2) 0.0391(6) Uani 1 1 d . . .
H19 H 0.3317 0.3240 -0.1913 0.052 Uiso 1 1 calc R . .
C20 C 0.1479(3) 0.26588(14) -0.2052(2) 0.0505(7) Uani 1 1 d . . .
H20 H 0.1349 0.2446 -0.2775 0.067 Uiso 1 1 calc R . .
C21 C 0.0515(3) 0.25064(14) -0.1476(3) 0.0547(8) Uani 1 1 d . . .
H21 H -0.0280 0.2190 -0.1817 0.073 Uiso 1 1 calc R . .
C22 C 0.0708(3) 0.28150(15) -0.0403(3) 0.0559(8) Uani 1 1 d . . .
H22 H 0.0053 0.2702 -0.0019 0.074 Uiso 1 1 calc R . .
C23 C 0.1875(2) 0.32936(13) 0.0110(2) 0.0431(7) Uani 1 1 d . . .
H23 H 0.2006 0.3501 0.0837 0.057 Uiso 1 1 calc R . .
O1 O 0.7204(2) 0.34043(12) 0.0304(2) 0.0864(8) Uani 1 1 d . . .
O2 O 1.00791(14) 0.47432(8) 0.24038(13) 0.0337(4) Uani 1 1 d . . .
O3 O 1.09199(14) 0.56542(8) 0.40892(13) 0.0337(4) Uani 1 1 d . . .
O4 O 0.71428(15) 0.66999(8) 0.53309(14) 0.0346(4) Uani 1 1 d . . .
O5 O 0.49769(13) 0.59282(8) 0.38284(13) 0.0289(4) Uani 1 1 d . . .
O6 O 0.42070(14) 0.48459(8) 0.23418(13) 0.0299(4) Uani 1 1 d . . .
O7 O 0.50391(14) 0.38133(8) 0.12110(13) 0.0313(4) Uani 1 1 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
C2 C1 C10 118.4(2) . . ?
C2 C1 C11 118.51(19) . . ?
C10 C1 C11 123.0(2) . . ?
O2 C2 C1 116.97(19) . . ?
O2 C2 C3 120.57(18) . . ?
C1 C2 C3 122.46(18) . . ?
C2 C3 C4 124.01(17) . . ?
C2 C3 C8 118.12(18) . . ?
C4 C3 C8 117.87(18) . . ?
O3 C4 C5 121.63(19) . . ?
O3 C4 C3 117.09(19) . . ?
C5 C4 C3 121.27(17) . . ?
C4 C5 C6 120.0(2) . . ?
O4 C6 C7 116.43(17) . . ?
O4 C6 C5 122.49(19) . . ?
C7 C6 C5 121.1(2) . . ?
C6 C7 O5 117.31(19) . . ?
C6 C7 C8 120.68(17) . . ?
O5 C7 C8 122.00(18) . . ?
C7 C8 C9 122.96(17) . . ?
C7 C8 C3 118.91(18) . . ?
C9 C8 C3 118.09(18) . . ?
C10 C9 O6 117.64(18) . . ?
C10 C9 C8 121.35(17) . . ?
O6 C9 C8 121.01(18) . . ?
C9 C10 O7 118.90(17) . . ?
C9 C10 C1 121.15(19) . . ?
O7 C10 C1 119.88(19) . . ?
O1 C11 C1 127.0(2) . . ?
O7 C17 C18 108.73(18) . . ?
C19 C18 C23 119.1(2) . . ?
C19 C18 C17 120.5(2) . . ?
C23 C18 C17 120.2(2) . . ?
C18 C19 C20 121.2(2) . . ?
C21 C20 C19 118.8(3) . . ?
C22 C21 C20 120.9(2) . . ?
C21 C22 C23 120.2(2) . . ?
C22 C23 C18 119.7(3) . . ?
C2 O2 C12 112.50(16) . . ?
C4 O3 C13 117.12(16) . . ?
C6 O4 C14 117.36(16) . . ?
C7 O5 C15 111.95(15) . . ?
C9 O6 C16 113.02(15) . . ?
C10 O7 C17 113.18(16) . . ?
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
C1 C2 1.382(3) . ?
C1 C10 1.423(3) . ?
C1 C11 1.469(3) . ?
C2 O2 1.378(2) . ?
C2 C3 1.421(3) . ?
C3 C4 1.430(3) . ?
C3 C8 1.443(2) . ?
C4 O3 1.362(2) . ?
C4 C5 1.371(3) . ?
C5 C6 1.400(3) . ?
C6 O4 1.362(2) . ?
C6 C7 1.374(3) . ?
C7 O5 1.392(2) . ?
C7 C8 1.413(3) . ?
C8 C9 1.432(3) . ?
C9 C10 1.364(3) . ?
C9 O6 1.380(2) . ?
C10 O7 1.380(2) . ?
C11 O1 1.192(3) . ?
C12 O2 1.446(3) . ?
C13 O3 1.440(2) . ?
C14 O4 1.428(3) . ?
C15 O5 1.429(2) . ?
C16 O6 1.441(2) . ?
C17 O7 1.434(2) . ?
C17 C18 1.504(3) . ?
C18 C19 1.378(3) . ?
C18 C23 1.390(3) . ?
C19 C20 1.390(3) . ?
C20 C21 1.373(3) . ?
C21 C22 1.373(4) . ?
C22 C23 1.385(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17249705
