#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/18/4021816.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_4021816
loop_
_publ_author_name
'Satoko Hayashi'
'Hideki Wada'
'Takashi Ueno'
'Waro Nakanishi'
_publ_section_title
;
 Structures of 1-(Arylseleninyl)naphthalenes: O, G, and Y Dependences
 in 8-G-1-[p-YC₆H₄Se(O)]C₁₀H₆
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5574
_journal_page_last               5585
_journal_paper_doi               10.1021/jo060527f
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C16 H11 Cl O Se '
_chemical_formula_sum            'C16 H11 Cl O Se'
_chemical_formula_weight         413.72
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             'Thu Dec  8 20:40:38 2005'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                106.35(1)
_cell_angle_beta                 97.32(1)
_cell_angle_gamma                84.94(1)
_cell_formula_units_Z            2
_cell_length_a                   9.167(1)
_cell_length_b                   10.057(2)
_cell_length_c                   7.759(1)
_cell_measurement_reflns_used    14
_cell_measurement_temperature    292.2
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      14.9
_cell_volume                     679.8(2)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        teXsan
_computing_publication_material  teXsan
_computing_structure_refinement  teXsan
_computing_structure_solution    SAPI91
_diffrn_ambient_temperature      292.2
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       ω-2θ
_diffrn_orient_matrix_UB_11      -0.07675
_diffrn_orient_matrix_UB_12      0.06151
_diffrn_orient_matrix_UB_13      -0.04764
_diffrn_orient_matrix_UB_21      -0.06775
_diffrn_orient_matrix_UB_22      -0.07817
_diffrn_orient_matrix_UB_23      -0.04131
_diffrn_orient_matrix_UB_31      -0.04066
_diffrn_orient_matrix_UB_32      0.02960
_diffrn_orient_matrix_UB_33      0.11947
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_av_sigmaI/netI    0.048
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3308
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.75
_diffrn_standards_decay_%        0.64
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.978
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.611
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_description       plate
_exptl_crystal_F_000             412.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.156
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0300
_refine_ls_shift/esd_max         0.0004
_refine_ls_shift/esd_mean        0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_obs         0.0314
_reflns_number_observed          2484
_reflns_number_total             3115
_reflns_observed_criterion       >1.5sigma(I)
_cod_data_source_file            jo060527fsi20060310_031129.cif
_cod_original_formula_sum        'C16 H11 Cl O Se '
_cod_database_code               4021816
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
Se(1) 0.85922(4) 0.41906(3) 0.32769(4) 0.03482(8) Uani d 1.00
Cl(1) 0.4570(1) 0.3196(1) -0.4364(1) 0.0593(3) Uani d 1.00
O(1) 0.9733(3) 0.5331(2) 0.3093(3) 0.0464(7) Uani d 1.00
C(1) 0.9778(3) 0.2444(3) 0.2676(4) 0.0357(8) Uani d 1.00
C(2) 1.1139(4) 0.2492(4) 0.2177(5) 0.0456(9) Uani d 1.00
C(3) 1.2061(4) 0.1261(4) 0.1783(5) 0.052(1) Uani d 1.00
C(4) 1.1588(4) 0.0049(4) 0.1901(5) 0.050(1) Uani d 1.00
C(5) 1.0192(4) -0.0014(3) 0.2433(4) 0.0416(8) Uani d 1.00
C(6) 0.9697(5) -0.1264(3) 0.2620(5) 0.052(1) Uani d 1.00
C(7) 0.8362(5) -0.1308(4) 0.3162(5) 0.055(1) Uani d 1.00
C(8) 0.7422(4) -0.0104(4) 0.3545(5) 0.050(1) Uani d 1.00
C(9) 0.7859(4) 0.1127(3) 0.3391(4) 0.0412(9) Uani d 1.00
C(10) 0.9241(3) 0.1209(3) 0.2836(4) 0.0353(8) Uani d 1.00
C(11) 0.7371(3) 0.3855(3) 0.0949(4) 0.0359(8) Uani d 1.00
C(12) 0.7867(4) 0.4221(4) -0.0434(5) 0.0421(9) Uani d 1.00
C(13) 0.7012(4) 0.4010(4) -0.2101(4) 0.0419(9) Uani d 1.00
C(14) 0.5662(3) 0.3443(3) -0.2297(4) 0.0404(8) Uani d 1.00
C(15) 0.5138(4) 0.3088(4) -0.0906(5) 0.0437(9) Uani d 1.00
C(16) 0.6014(4) 0.3300(4) 0.0741(4) 0.0419(9) Uani d 1.00
H(1) 1.1427 0.3371 0.2099 0.0629 Uiso calc 1.00
H(2) 1.3050 0.1363 0.1358 0.0629 Uiso calc 1.00
H(3) 1.2234 -0.0908 0.1643 0.0629 Uiso calc 1.00
H(4) 1.0375 -0.2223 0.2419 0.0629 Uiso calc 1.00
H(5) 0.8255 -0.2339 0.3342 0.0629 Uiso calc 1.00
H(6) 0.6461 -0.0263 0.3843 0.0629 Uiso calc 1.00
H(7) 0.7237 0.2010 0.3731 0.0629 Uiso calc 1.00
H(8) 0.8772 0.4650 -0.0332 0.0629 Uiso calc 1.00
H(9) 0.7404 0.4384 -0.3154 0.0629 Uiso calc 1.00
H(10) 0.4284 0.2416 -0.1267 0.0629 Uiso calc 1.00
H(11) 0.5607 0.3040 0.1772 0.0629 Uiso calc 1.00
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 32 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0 22 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O 0 2 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
Cl 0 2 0.148 0.159
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
Se 0 2 -0.093 2.226
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 0 1
-2 0 1
-2 1 1
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O(1) Se(1) C(1) 102.4(1) 1_555 1_555 1_555 yes
O(1) Se(1) C(11) 101.6(1) 1_555 1_555 1_555 yes
C(1) Se(1) C(11) 95.9(1) 1_555 1_555 1_555 yes
Se(1) C(1) C(2) 117.0(2) 1_555 1_555 1_555 yes
Se(1) C(1) C(10) 120.3(2) 1_555 1_555 1_555 yes
C(2) C(1) C(10) 122.7(3) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 119.2(3) 1_555 1_555 1_555 yes
C(1) C(2) H(1) 117.9(3) 1_555 1_555 1_555 no
C(3) C(2) H(1) 123.0(4) 1_555 1_555 1_555 no
C(2) C(3) C(4) 120.3(3) 1_555 1_555 1_555 yes
C(2) C(3) H(2) 114.9(4) 1_555 1_555 1_555 no
C(4) C(3) H(2) 124.7(4) 1_555 1_555 1_555 no
C(3) C(4) C(5) 121.2(3) 1_555 1_555 1_555 yes
C(3) C(4) H(3) 123.9(4) 1_555 1_555 1_555 no
C(5) C(4) H(3) 114.8(4) 1_555 1_555 1_555 no
C(4) C(5) C(6) 122.0(3) 1_555 1_555 1_555 yes
C(4) C(5) C(10) 119.7(3) 1_555 1_555 1_555 yes
C(6) C(5) C(10) 118.3(3) 1_555 1_555 1_555 yes
C(5) C(6) C(7) 121.5(3) 1_555 1_555 1_555 yes
C(5) C(6) H(4) 123.1(4) 1_555 1_555 1_555 no
C(7) C(6) H(4) 115.3(4) 1_555 1_555 1_555 no
C(6) C(7) C(8) 120.0(3) 1_555 1_555 1_555 yes
C(6) C(7) H(5) 109.2(4) 1_555 1_555 1_555 no
C(8) C(7) H(5) 130.5(4) 1_555 1_555 1_555 no
C(7) C(8) C(9) 120.4(4) 1_555 1_555 1_555 yes
C(7) C(8) H(6) 113.4(3) 1_555 1_555 1_555 no
C(9) C(8) H(6) 126.1(4) 1_555 1_555 1_555 no
C(8) C(9) C(10) 121.0(3) 1_555 1_555 1_555 yes
C(8) C(9) H(7) 121.8(3) 1_555 1_555 1_555 no
C(10) C(9) H(7) 117.1(3) 1_555 1_555 1_555 no
C(1) C(10) C(5) 117.0(3) 1_555 1_555 1_555 yes
C(1) C(10) C(9) 124.3(3) 1_555 1_555 1_555 yes
C(5) C(10) C(9) 118.7(3) 1_555 1_555 1_555 yes
Se(1) C(11) C(12) 118.8(2) 1_555 1_555 1_555 yes
Se(1) C(11) C(16) 120.1(2) 1_555 1_555 1_555 yes
C(12) C(11) C(16) 121.0(3) 1_555 1_555 1_555 yes
C(11) C(12) C(13) 120.1(3) 1_555 1_555 1_555 yes
C(11) C(12) H(8) 123.9(3) 1_555 1_555 1_555 no
C(13) C(12) H(8) 116.0(3) 1_555 1_555 1_555 no
C(12) C(13) C(14) 118.3(3) 1_555 1_555 1_555 yes
C(12) C(13) H(9) 118.3(3) 1_555 1_555 1_555 no
C(14) C(13) H(9) 123.2(3) 1_555 1_555 1_555 no
Cl(1) C(14) C(13) 118.8(3) 1_555 1_555 1_555 yes
Cl(1) C(14) C(15) 119.0(3) 1_555 1_555 1_555 yes
C(13) C(14) C(15) 122.2(3) 1_555 1_555 1_555 yes
C(14) C(15) C(16) 118.5(3) 1_555 1_555 1_555 yes
C(14) C(15) H(10) 116.4(3) 1_555 1_555 1_555 no
C(16) C(15) H(10) 122.4(3) 1_555 1_555 1_555 no
C(11) C(16) C(15) 119.9(3) 1_555 1_555 1_555 yes
C(11) C(16) H(11) 122.4(3) 1_555 1_555 1_555 no
C(15) C(16) H(11) 117.8(3) 1_555 1_555 1_555 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se(1) O(1) 1.665(2) 1_555 1_555 yes
Se(1) C(1) 1.953(3) 1_555 1_555 yes
Se(1) C(11) 1.959(3) 1_555 1_555 yes
Cl(1) C(14) 1.745(3) 1_555 1_555 yes
C(1) C(2) 1.361(4) 1_555 1_555 yes
C(1) C(10) 1.418(4) 1_555 1_555 yes
C(2) C(3) 1.418(5) 1_555 1_555 yes
C(3) C(4) 1.359(6) 1_555 1_555 yes
C(4) C(5) 1.406(5) 1_555 1_555 yes
C(5) C(6) 1.424(5) 1_555 1_555 yes
C(5) C(10) 1.427(4) 1_555 1_555 yes
C(6) C(7) 1.352(6) 1_555 1_555 yes
C(7) C(8) 1.405(5) 1_555 1_555 yes
C(8) C(9) 1.375(4) 1_555 1_555 yes
C(9) C(10) 1.406(4) 1_555 1_555 yes
C(11) C(12) 1.368(4) 1_555 1_555 yes
C(11) C(16) 1.380(4) 1_555 1_555 yes
C(12) C(13) 1.396(4) 1_555 1_555 yes
C(13) C(14) 1.381(4) 1_555 1_555 yes
C(14) C(15) 1.379(5) 1_555 1_555 yes
C(15) C(16) 1.392(4) 1_555 1_555 yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Se(1) O(1) 2.965(2) 1_555 2_766
O(1) O(1) 3.182(5) 1_555 2_766
O(1) C(12) 3.340(4) 1_555 2_765
O(1) C(13) 3.340(4) 1_555 2_765
O(1) C(1) 3.413(4) 1_555 2_766
O(1) C(7) 3.489(4) 1_555 1_565
O(1) C(6) 3.542(4) 1_555 1_565
C(2) C(6) 3.580(5) 1_555 2_755
C(3) C(6) 3.588(5) 1_555 2_755
C(4) C(8) 3.520(5) 1_555 2_756
C(4) C(5) 3.538(4) 1_555 2_755
C(4) C(10) 3.539(4) 1_555 2_755
C(5) C(7) 3.436(5) 1_555 2_756
C(5) C(8) 3.555(5) 1_555 2_756
C(6) C(10) 3.522(4) 1_555 2_756
C(6) C(9) 3.558(5) 1_555 2_756
C(7) C(10) 3.551(4) 1_555 2_756
C(14) C(16) 3.451(5) 1_555 2_665
