#------------------------------------------------------------------------------
#$Date: 2016-10-19 04:33:43 +0300 (Wed, 19 Oct 2016) $
#$Revision: 187411 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/43/1544311.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_1544311
loop_
_publ_author_name
'Madan Kumar, S.'
'Manju, N.'
'Kalluraya, Balakrishna'
'Byrappa, K.'
'Abdoh, M. M. M.'
_publ_section_title
;
 Ethyl (naphthalen-2-yloxy)acetate
;
_journal_coeditor_code           HB4083
_journal_issue                   10
_journal_name_full               IUCrData
_journal_page_first              x161594
_journal_paper_doi               10.1107/S2414314616015947
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C14 H14 O3'
_chemical_formula_moiety         'C14 H14 O3'
_chemical_formula_sum            'C14 H14 O3'
_chemical_formula_weight         230.25
_chemical_name_systematic
;
Ethyl (naphthalen-2-yloxy)acetate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                106.062(12)
_cell_angle_beta                 102.923(14)
_cell_angle_gamma                103.358(14)
_cell_formula_units_Z            2
_cell_length_a                   6.0504(11)
_cell_length_b                   10.2188(13)
_cell_length_c                   10.8744(16)
_cell_measurement_reflns_used    2265
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      2.2
_cell_volume                     598.14(18)
_computing_cell_refinement
;
CrystalClear SM Expert (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear SM Expert (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear SM Expert (Rigaku, 2011)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ CCD'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6262
_diffrn_reflns_theta_full        25.672
_diffrn_reflns_theta_max         25.672
_diffrn_reflns_theta_min         2.183
_diffrn_standards_number         2265
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(NUMABS; Rigaku, 1999)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1633
_refine_ls_R_factor_gt           0.0827
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1130P)²+0.0443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1993
_refine_ls_wR_factor_ref         0.2589
_reflns_number_gt                1133
_reflns_number_total             2265
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4083sup1.cif
_cod_data_source_block           I245
_cod_original_cell_volume        598.15(17)
_cod_database_code               1544311
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.970
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
O O1 0.2337(4) 0.3569(3) 0.9618(2) 0.0765(8) Uani d 1
O O2 0.2739(5) 0.4668(3) 0.7673(3) 0.0915(10) Uani d 1
O O3 0.5040(5) 0.3364(3) 0.7049(2) 0.0783(9) Uani d 1
C C1 0.0300(6) 0.3263(4) 1.1143(4) 0.0719(11) Uani d 1
H H1 -0.0336 0.3969 1.0988 0.086 Uiso calc 1
C C2 -0.0308(6) 0.2642(4) 1.2017(4) 0.0755(11) Uani d 1
H H2 -0.1382 0.2915 1.2446 0.091 Uiso calc 1
C C3 0.0669(6) 0.1581(4) 1.2292(4) 0.0692(10) Uani d 1
C C4 0.0083(7) 0.0897(4) 1.3181(4) 0.0823(12) Uani d 1
H H4 -0.1001 0.1136 1.3618 0.099 Uiso calc 1
C C5 0.1070(8) -0.0108(5) 1.3414(4) 0.0904(13) Uani d 1
H H5 0.0686 -0.0533 1.4025 0.108 Uiso calc 1
C C6 0.2645(8) -0.0510(4) 1.2754(4) 0.0896(13) Uani d 1
H H6 0.3278 -0.1220 1.2903 0.108 Uiso calc 1
C C7 0.3263(7) 0.0129(4) 1.1895(4) 0.0789(12) Uani d 1
H H7 0.4360 -0.0125 1.1476 0.095 Uiso calc 1
C C8 0.2261(6) 0.1186(4) 1.1622(3) 0.0641(10) Uani d 1
C C9 0.2891(6) 0.1861(4) 1.0725(4) 0.0679(10) Uani d 1
H H9 0.4001 0.1629 1.0307 0.082 Uiso calc 1
C C10 0.1873(6) 0.2851(4) 1.0473(3) 0.0626(9) Uani d 1
C C11 0.3813(6) 0.3139(4) 0.8862(3) 0.0696(10) Uani d 1
H H11A 0.3247 0.2105 0.8429 0.084 Uiso calc 1
H H11B 0.5432 0.3412 0.9450 0.084 Uiso calc 1
C C12 0.3782(6) 0.3843(4) 0.7817(3) 0.0672(10) Uani d 1
C C13 0.5213(7) 0.3934(4) 0.5988(4) 0.0809(12) Uani d 1
H H13A 0.5844 0.4972 0.6355 0.097 Uiso calc 1
H H13B 0.3649 0.3663 0.5341 0.097 Uiso calc 1
C C14 0.6823(7) 0.3339(5) 0.5331(4) 0.1014(15) Uani d 1
H H14A 0.6934 0.3679 0.4600 0.152 Uiso calc 1
H H14B 0.6205 0.2311 0.4992 0.152 Uiso calc 1
H H14C 0.8380 0.3640 0.5972 0.152 Uiso calc 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
C10 O1 C11 116.5(2)
C12 O3 C13 117.0(3)
C2 C1 H1 119.8
C2 C1 C10 120.4(3)
C10 C1 H1 119.8
C1 C2 H2 119.5
C1 C2 C3 121.0(3)
C3 C2 H2 119.5
C4 C3 C2 123.2(3)
C8 C3 C2 118.1(3)
C8 C3 C4 118.7(3)
C3 C4 H4 119.5
C5 C4 C3 121.0(4)
C5 C4 H4 119.5
C4 C5 H5 119.6
C4 C5 C6 120.7(4)
C6 C5 H5 119.6
C5 C6 H6 120.0
C7 C6 C5 120.0(4)
C7 C6 H6 120.0
C6 C7 H7 119.6
C6 C7 C8 120.9(4)
C8 C7 H7 119.6
C3 C8 C7 118.6(3)
C3 C8 C9 119.9(3)
C9 C8 C7 121.5(3)
C8 C9 H9 120.1
C10 C9 C8 119.9(3)
C10 C9 H9 120.1
O1 C10 C1 114.3(3)
C9 C10 O1 125.0(3)
C9 C10 C1 120.7(3)
O1 C11 H11A 109.8
O1 C11 H11B 109.8
O1 C11 C12 109.3(3)
H11A C11 H11B 108.3
C12 C11 H11A 109.8
C12 C11 H11B 109.8
O2 C12 O3 125.0(4)
O2 C12 C11 125.7(3)
O3 C12 C11 109.3(3)
O3 C13 H13A 110.2
O3 C13 H13B 110.2
O3 C13 C14 107.7(3)
H13A C13 H13B 108.5
C14 C13 H13A 110.2
C14 C13 H13B 110.2
C13 C14 H14A 109.5
C13 C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14B 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C10 1.372(4)
O1 C11 1.406(4)
O2 C12 1.187(4)
O3 C12 1.322(4)
O3 C13 1.442(4)
C1 H1 0.9300
C1 C2 1.350(5)
C1 C10 1.393(4)
C2 H2 0.9300
C2 C3 1.418(5)
C3 C4 1.402(5)
C3 C8 1.397(5)
C4 H4 0.9300
C4 C5 1.355(5)
C5 H5 0.9300
C5 C6 1.384(5)
C6 H6 0.9300
C6 C7 1.349(5)
C7 H7 0.9300
C7 C8 1.421(5)
C8 C9 1.411(5)
C9 H9 0.9300
C9 C10 1.358(5)
C11 H11A 0.9700
C11 H11B 0.9700
C11 C12 1.502(5)
C13 H13A 0.9700
C13 H13B 0.9700
C13 C14 1.474(5)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
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
O1 C11 C12 O2 2.2(5)
O1 C11 C12 O3 -175.8(3)
C1 C2 C3 C4 -179.5(4)
C1 C2 C3 C8 -0.6(6)
C2 C1 C10 O1 -179.9(3)
C2 C1 C10 C9 -2.5(6)
C2 C3 C4 C5 -179.8(4)
C2 C3 C8 C7 179.6(3)
C2 C3 C8 C9 1.4(6)
C3 C4 C5 C6 -1.5(7)
C3 C8 C9 C10 -2.7(6)
C4 C3 C8 C7 -1.5(6)
C4 C3 C8 C9 -179.7(3)
C4 C5 C6 C7 1.8(7)
C5 C6 C7 C8 -1.9(6)
C6 C7 C8 C3 1.8(6)
C6 C7 C8 C9 -180.0(4)
C7 C8 C9 C10 179.1(3)
C8 C3 C4 C5 1.4(6)
C8 C9 C10 O1 -179.6(3)
C8 C9 C10 C1 3.3(6)
C10 O1 C11 C12 170.1(3)
C10 C1 C2 C3 1.2(6)
C11 O1 C10 C1 -176.7(3)
C11 O1 C10 C9 6.1(5)
C12 O3 C13 C14 176.0(3)
C13 O3 C12 O2 2.2(6)
C13 O3 C12 C11 -179.7(3)
