#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/59/2225996.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_2225996
loop_
_publ_author_name
'Bibi, Uzma'
'Siddiqi, Humaira M.'
'Akhter, Zareen'
'Bolte, Michael'
_publ_section_title
;
 4-Nitrophenyl 1-naphthoate
;
_journal_coeditor_code           TK2650
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1023
_journal_paper_doi               10.1107/S1600536810011736
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H11 N O4'
_chemical_formula_moiety         'C17 H11 N O4'
_chemical_formula_sum            'C17 H11 N O4'
_chemical_formula_weight         293.27
_chemical_name_systematic
;
4-Nitrophenyl 1-naphthoate
;
_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_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                 99.006(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2049(6)
_cell_length_b                   12.8175(8)
_cell_length_c                   14.7838(14)
_cell_measurement_reflns_used    8709
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      3.3
_cell_volume                     1348.44(19)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Stoe IPDS-II two-circle'
_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  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10239
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.61
_diffrn_reflns_theta_min         3.27
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.199
_refine_ls_extinction_coef       0.0103(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0344
_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)+(0.0582P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                1928
_reflns_number_total             2508
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2650.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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225996
_cod_database_fobs_code          2225996
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.36959(17) 0.15975(9) 0.73346(9) 0.0357(3) Uani d . 1 . .
O O1 0.28241(13) 0.47946(6) 0.47417(6) 0.0264(2) Uani d . 1 . .
O O2 0.14518(13) 0.59160(7) 0.56191(7) 0.0303(2) Uani d . 1 . .
O O3 0.42873(18) 0.18063(9) 0.81407(8) 0.0526(3) Uani d . 1 . .
O O4 0.33027(18) 0.07066(8) 0.70625(9) 0.0519(3) Uani d . 1 . .
C C1 0.19783(17) 0.57191(9) 0.49057(9) 0.0239(3) Uani d . 1 . .
C C2 0.30357(17) 0.40273(9) 0.54233(9) 0.0239(3) Uani d . 1 . .
C C3 0.38432(18) 0.42424(10) 0.63163(10) 0.0275(3) Uani d . 1 . .
H H3 0.4249 0.4929 0.6491 0.033 Uiso calc R 1 . .
C C4 0.40489(18) 0.34404(10) 0.69505(10) 0.0291(3) Uani d . 1 . .
H H4 0.4579 0.3568 0.7570 0.035 Uiso calc R 1 . .
C C5 0.34691(18) 0.24492(10) 0.66653(9) 0.0272(3) Uani d . 1 . .
C C6 0.27048(19) 0.22251(10) 0.57696(10) 0.0301(3) Uani d . 1 . .
H H6 0.2335 0.1534 0.5592 0.036 Uiso calc R 1 . .
C C7 0.24893(19) 0.30293(10) 0.51368(10) 0.0280(3) Uani d . 1 . .
H H7 0.1975 0.2899 0.4516 0.034 Uiso calc R 1 . .
C C11 0.17730(17) 0.63938(10) 0.40772(9) 0.0239(3) Uani d . 1 . .
C C12 0.20200(17) 0.75036(9) 0.41572(9) 0.0250(3) Uani d . 1 . .
C C13 0.2570(2) 0.80306(10) 0.49996(10) 0.0323(3) Uani d . 1 . .
H H13 0.2770 0.7646 0.5556 0.039 Uiso calc R 1 . .
C C14 0.2816(2) 0.90913(11) 0.50176(12) 0.0426(4) Uani d . 1 . .
H H14 0.3169 0.9436 0.5588 0.051 Uiso calc R 1 . .
C C15 0.2553(2) 0.96756(11) 0.42033(13) 0.0460(4) Uani d . 1 . .
H H15 0.2738 1.0410 0.4226 0.055 Uiso calc R 1 . .
C C16 0.2035(2) 0.91929(11) 0.33809(12) 0.0380(4) Uani d . 1 . .
H H16 0.1867 0.9594 0.2834 0.046 Uiso calc R 1 . .
C C17 0.17434(18) 0.80981(10) 0.33332(10) 0.0286(3) Uani d . 1 . .
C C18 0.12013(19) 0.75958(11) 0.24776(10) 0.0322(3) Uani d . 1 . .
H H18 0.0998 0.8000 0.1932 0.039 Uiso calc R 1 . .
C C19 0.0969(2) 0.65407(11) 0.24282(10) 0.0334(3) Uani d . 1 . .
H H19 0.0601 0.6213 0.1851 0.040 Uiso calc R 1 . .
C C20 0.12749(19) 0.59370(10) 0.32339(10) 0.0288(3) Uani d . 1 . .
H H20 0.1134 0.5201 0.3193 0.035 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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O4 N1 O3 . . 123.10(12) ?
O4 N1 C5 . . 118.41(13) ?
O3 N1 C5 . . 118.49(12) ?
C1 O1 C2 . . 118.78(10) ?
O2 C1 O1 . . 123.12(12) ?
O2 C1 C11 . . 126.58(11) ?
O1 C1 C11 . . 110.27(11) ?
C3 C2 C7 . . 122.17(12) ?
C3 C2 O1 . . 121.92(11) ?
C7 C2 O1 . . 115.80(12) ?
C4 C3 C2 . . 118.86(12) ?
C4 C3 H3 . . 120.6 ?
C2 C3 H3 . . 120.6 ?
C5 C4 C3 . . 118.75(13) ?
C5 C4 H4 . . 120.6 ?
C3 C4 H4 . . 120.6 ?
C4 C5 C6 . . 122.62(12) ?
C4 C5 N1 . . 118.84(13) ?
C6 C5 N1 . . 118.53(12) ?
C5 C6 C7 . . 118.57(12) ?
C5 C6 H6 . . 120.7 ?
C7 C6 H6 . . 120.7 ?
C6 C7 C2 . . 118.99(13) ?
C6 C7 H7 . . 120.5 ?
C2 C7 H7 . . 120.5 ?
C20 C11 C12 . . 120.56(12) ?
C20 C11 C1 . . 118.54(11) ?
C12 C11 C1 . . 120.86(12) ?
C13 C12 C17 . . 118.61(12) ?
C13 C12 C11 . . 123.94(12) ?
C17 C12 C11 . . 117.43(12) ?
C14 C13 C12 . . 120.47(14) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C15 . . 120.82(15) ?
C13 C14 H14 . . 119.6 ?
C15 C14 H14 . . 119.6 ?
C16 C15 C14 . . 120.24(14) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 C17 . . 120.72(14) ?
C15 C16 H16 . . 119.6 ?
C17 C16 H16 . . 119.6 ?
C18 C17 C16 . . 120.73(13) ?
C18 C17 C12 . . 120.13(12) ?
C16 C17 C12 . . 119.13(13) ?
C19 C18 C17 . . 120.82(13) ?
C19 C18 H18 . . 119.6 ?
C17 C18 H18 . . 119.6 ?
C18 C19 C20 . . 119.87(13) ?
C18 C19 H19 . . 120.1 ?
C20 C19 H19 . . 120.1 ?
C11 C20 C19 . . 121.17(12) ?
C11 C20 H20 . . 119.4 ?
C19 C20 H20 . . 119.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 O4 . 1.2290(16) ?
N1 O3 . 1.2307(18) ?
N1 C5 . 1.4651(17) ?
O1 C1 . 1.3713(15) ?
O1 C2 . 1.3993(15) ?
O2 C1 . 1.2022(17) ?
C1 C11 . 1.4876(18) ?
C2 C3 . 1.385(2) ?
C2 C7 . 1.3850(18) ?
C3 C4 . 1.3836(19) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3825(19) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.382(2) ?
C6 C7 . 1.3844(19) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C11 C20 . 1.373(2) ?
C11 C12 . 1.4362(18) ?
C12 C13 . 1.418(2) ?
C12 C17 . 1.4242(19) ?
C13 C14 . 1.371(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.405(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.363(2) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.4191(19) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.419(2) ?
C18 C19 . 1.363(2) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.409(2) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C18 H18 O2 4_575 0.9500 2.4500 3.3728(18) 164.00 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 O1 C1 O2 . . . . 2.09(18) ?
C2 O1 C1 C11 . . . . -176.10(10) ?
C1 O1 C2 C3 . . . . -51.49(16) ?
C1 O1 C2 C7 . . . . 132.16(12) ?
C7 C2 C3 C4 . . . . -2.4(2) ?
O1 C2 C3 C4 . . . . -178.48(12) ?
C2 C3 C4 C5 . . . . 1.1(2) ?
C3 C4 C5 C6 . . . . 0.5(2) ?
C3 C4 C5 N1 . . . . 179.64(12) ?
O4 N1 C5 C4 . . . . -174.87(13) ?
O3 N1 C5 C4 . . . . 4.5(2) ?
O4 N1 C5 C6 . . . . 4.29(19) ?
O3 N1 C5 C6 . . . . -176.38(13) ?
C4 C5 C6 C7 . . . . -0.9(2) ?
N1 C5 C6 C7 . . . . 179.98(12) ?
C5 C6 C7 C2 . . . . -0.3(2) ?
C3 C2 C7 C6 . . . . 2.0(2) ?
O1 C2 C7 C6 . . . . 178.32(12) ?
O2 C1 C11 C20 . . . . -138.43(14) ?
O1 C1 C11 C20 . . . . 39.68(15) ?
O2 C1 C11 C12 . . . . 39.26(19) ?
O1 C1 C11 C12 . . . . -142.63(11) ?
C20 C11 C12 C13 . . . . -178.63(13) ?
C1 C11 C12 C13 . . . . 3.73(19) ?
C20 C11 C12 C17 . . . . -0.49(18) ?
C1 C11 C12 C17 . . . . -178.13(11) ?
C17 C12 C13 C14 . . . . 0.4(2) ?
C11 C12 C13 C14 . . . . 178.56(14) ?
C12 C13 C14 C15 . . . . -0.8(2) ?
C13 C14 C15 C16 . . . . 0.4(3) ?
C14 C15 C16 C17 . . . . 0.3(2) ?
C15 C16 C17 C18 . . . . 179.92(14) ?
C15 C16 C17 C12 . . . . -0.7(2) ?
C13 C12 C17 C18 . . . . 179.70(12) ?
C11 C12 C17 C18 . . . . 1.46(18) ?
C13 C12 C17 C16 . . . . 0.31(19) ?
C11 C12 C17 C16 . . . . -177.93(12) ?
C16 C17 C18 C19 . . . . 178.26(14) ?
C12 C17 C18 C19 . . . . -1.1(2) ?
C17 C18 C19 C20 . . . . -0.2(2) ?
C12 C11 C20 C19 . . . . -0.8(2) ?
C1 C11 C20 C19 . . . . 176.85(12) ?
C18 C19 C20 C11 . . . . 1.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 463931
