#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/91/2209102.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2209102
loop_
_publ_author_name
'Lin-Hai Jing'
'Da-Bin Qin'
'Huan-Xia Zhang'
'Shao-Jin Gu'
'Zhi-Hua Mao'
_publ_section_title
;
 Diethyl naphthalene-1,4-dicarboxylate
;
_journal_coeditor_code           BT2075
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2300
_journal_page_last               o2301
_journal_paper_doi               10.1107/S1600536806017119
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H16 O4'
_chemical_formula_moiety         'C16 H16 O4'
_chemical_formula_sum            'C16 H16 O4'
_chemical_formula_weight         272.29
_chemical_name_systematic
;
Diethyl naphthalene-1,4-dicarboxylate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 95.277(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.731(7)
_cell_length_b                   7.2792(16)
_cell_length_c                   16.151(4)
_cell_measurement_reflns_used    33
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.75
_cell_measurement_theta_min      3.15
_cell_volume                     2895.2(13)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia,1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_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  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2632
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.65
_diffrn_standards_decay_%        3.25
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.401
_refine_ls_extinction_coef       0.0144(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2569
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0643
_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)+(0.091P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1725
_reflns_number_gt                1400
_reflns_number_total             2569
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2075.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2209102
_cod_database_fobs_code          2209102
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.38480(7) 0.5421(3) 0.43238(12) 0.0780(7) Uani d . 1
O O2 0.40796(9) 0.4634(4) 0.56335(13) 0.0950(8) Uani d . 1
O O3 0.11616(8) 0.5334(3) 0.44940(12) 0.0782(6) Uani d . 1
O O4 0.11771(9) 0.4472(4) 0.58165(13) 0.0931(8) Uani d . 1
C C1 0.31396(10) 0.5112(3) 0.51650(15) 0.0507(6) Uani d . 1
C C2 0.27985(11) 0.4613(3) 0.44841(14) 0.0522(7) Uani d . 1
H H2 0.2943 0.4279 0.3994 0.063 Uiso calc R 1
C C3 0.22389(11) 0.4600(3) 0.45176(15) 0.0530(7) Uani d . 1
H H3 0.2015 0.4245 0.4051 0.064 Uiso calc R 1
C C4 0.20122(10) 0.5095(3) 0.52211(15) 0.0500(6) Uani d . 1
C C5 0.21361(11) 0.6430(4) 0.66549(15) 0.0590(7) Uani d . 1
H H5 0.1762 0.6445 0.6684 0.071 Uiso calc R 1
C C6 0.24699(13) 0.7109(4) 0.72981(15) 0.0669(8) Uani d . 1
H H6 0.2321 0.7608 0.7757 0.080 Uiso calc R 1
C C7 0.30319(13) 0.7067(4) 0.72788(16) 0.0699(8) Uani d . 1
H H7 0.3256 0.7516 0.7727 0.084 Uiso calc R 1
C C8 0.32509(11) 0.6376(4) 0.66107(15) 0.0619(7) Uani d . 1
H H8 0.3627 0.6351 0.6607 0.074 Uiso calc R 1
C C9 0.29228(10) 0.5686(3) 0.59151(14) 0.0504(7) Uani d . 1
C C10 0.23506(11) 0.5701(3) 0.59411(14) 0.0499(6) Uani d . 1
C C11 0.37372(12) 0.5038(4) 0.50941(18) 0.0644(8) Uani d . 1
C C12 0.44059(13) 0.5208(6) 0.4157(2) 0.1036(12) Uani d D 1
H H12A 0.4523 0.3952 0.4264 0.124 Uiso calc R 1
H H12B 0.4636 0.6018 0.4513 0.124 Uiso calc R 1
C C13 0.44423(17) 0.5673(10) 0.3283(2) 0.191(3) Uani d D 1
H H13A 0.4275 0.4721 0.2937 0.229 Uiso calc R 1
H H13B 0.4817 0.5787 0.3180 0.229 Uiso calc R 1
H H13C 0.4259 0.6816 0.3158 0.229 Uiso calc R 1
C C14 0.14138(12) 0.4937(4) 0.52399(18) 0.0639(7) Uani d . 1
C C15 0.05814(12) 0.5075(6) 0.4401(2) 0.0987(12) Uani d D 1
H H15A 0.0408 0.5908 0.4764 0.118 Uiso calc R 1
H H15B 0.0492 0.3825 0.4546 0.118 Uiso calc R 1
C C16 0.03919(17) 0.5448(9) 0.3526(2) 0.169(2) Uani d D 1
H H16A 0.0497 0.6669 0.3382 0.203 Uiso calc R 1
H H16B 0.0004 0.5343 0.3450 0.203 Uiso calc R 1
H H16C 0.0552 0.4577 0.3174 0.203 Uiso calc R 1
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_publ_flag
C11 O1 C12 115.9(2) y
C14 O3 C15 116.3(2) y
C2 C1 C9 120.3(2) ?
C2 C1 C11 117.9(2) ?
C9 C1 C11 121.7(2) ?
C1 C2 C3 120.8(2) ?
C1 C2 H2 119.6 ?
C3 C2 H2 119.6 ?
C4 C3 C2 121.2(2) ?
C4 C3 H3 119.4 ?
C2 C3 H3 119.4 ?
C3 C4 C10 120.2(2) ?
C3 C4 C14 118.9(2) ?
C10 C4 C14 120.9(2) ?
C6 C5 C10 120.8(3) ?
C6 C5 H5 119.6 ?
C10 C5 H5 119.6 ?
C5 C6 C7 120.8(3) ?
C5 C6 H6 119.6 ?
C7 C6 H6 119.6 ?
C8 C7 C6 120.1(3) ?
C8 C7 H7 120.0 ?
C6 C7 H7 120.0 ?
C7 C8 C9 121.6(3) ?
C7 C8 H8 119.2 ?
C9 C8 H8 119.2 ?
C8 C9 C10 118.3(2) ?
C8 C9 C1 122.9(2) ?
C10 C9 C1 118.6(2) ?
C5 C10 C9 118.4(2) ?
C5 C10 C4 122.7(2) ?
C9 C10 C4 118.8(2) ?
O2 C11 O1 122.8(3) ?
O2 C11 C1 126.4(3) ?
O1 C11 C1 110.8(2) ?
O1 C12 C13 107.5(3) ?
O1 C12 H12A 110.2 ?
C13 C12 H12A 110.2 ?
O1 C12 H12B 110.2 ?
C13 C12 H12B 110.2 ?
H12A C12 H12B 108.5 ?
C12 C13 H13A 109.5 ?
C12 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C12 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
O4 C14 O3 122.9(3) ?
O4 C14 C4 126.7(3) ?
O3 C14 C4 110.3(2) ?
O3 C15 C16 107.6(3) ?
O3 C15 H15A 110.2 ?
C16 C15 H15A 110.2 ?
O3 C15 H15B 110.2 ?
C16 C15 H15B 110.2 ?
H15A C15 H15B 108.5 ?
C15 C16 H16A 109.5 ?
C15 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C15 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 1.328(3) y
O1 C12 1.438(3) y
O2 C11 1.194(3) y
O3 C14 1.336(3) y
O3 C15 1.441(4) y
O4 C14 1.194(3) y
C1 C2 1.372(3) ?
C1 C9 1.432(3) ?
C1 C11 1.494(4) ?
C2 C3 1.390(3) ?
C2 H2 0.9300 ?
C3 C4 1.361(3) ?
C3 H3 0.9300 ?
C4 C10 1.438(3) ?
C4 C14 1.487(4) ?
C5 C6 1.359(4) ?
C5 C10 1.416(3) ?
C5 H5 0.9300 ?
C6 C7 1.393(4) ?
C6 H6 0.9300 ?
C7 C8 1.348(4) ?
C7 H7 0.9300 ?
C8 C9 1.416(3) ?
C8 H8 0.9300 ?
C9 C10 1.420(3) ?
C12 C13 1.463(3) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C15 C16 1.473(3) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5 O4 0.93 2.40 2.983(3) 121
C8 H8 O2 0.93 2.37 2.982(4) 123
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C9 C1 C2 C3 -2.0(4)
C11 C1 C2 C3 178.1(2)
C1 C2 C3 C4 0.6(4)
C2 C3 C4 C10 1.9(4)
C2 C3 C4 C14 -176.0(2)
C10 C5 C6 C7 -1.4(4)
C5 C6 C7 C8 1.1(4)
C6 C7 C8 C9 0.2(4)
C7 C8 C9 C10 -1.3(4)
C7 C8 C9 C1 173.7(2)
C2 C1 C9 C8 -174.1(2)
C11 C1 C9 C8 5.9(4)
C2 C1 C9 C10 0.9(3)
C11 C1 C9 C10 -179.2(2)
C6 C5 C10 C9 0.3(4)
C6 C5 C10 C4 -175.2(2)
C8 C9 C10 C5 1.0(3)
C1 C9 C10 C5 -174.2(2)
C8 C9 C10 C4 176.7(2)
C1 C9 C10 C4 1.5(3)
C3 C4 C10 C5 172.6(2)
C14 C4 C10 C5 -9.5(4)
C3 C4 C10 C9 -2.9(3)
C14 C4 C10 C9 174.9(2)
C12 O1 C11 O2 3.8(5)
C12 O1 C11 C1 -173.9(3)
C2 C1 C11 O2 -145.2(3)
C9 C1 C11 O2 34.9(4)
C2 C1 C11 O1 32.4(3)
C9 C1 C11 O1 -147.5(2)
C11 O1 C12 C13 179.5(4)
C15 O3 C14 O4 -3.3(4)
C15 O3 C14 C4 174.6(3)
C3 C4 C14 O4 142.4(3)
C10 C4 C14 O4 -35.5(4)
C3 C4 C14 O3 -35.4(3)
C10 C4 C14 O3 146.8(2)
C14 O3 C15 C16 -175.7(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9623509
