#------------------------------------------------------------------------------
#$Date: 2019-11-28 18:59:52 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244366 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/88/7238806.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_7238806
loop_
_publ_author_name
'Seike, Aya'
'Yamagami, Kaoru'
'Kakitani, Yoshimasa'
'Kuwajima, Miki'
'Uoyama, Hiroki'
'Nagaoka, Shin-ichi'
'Nakae, Takahiro'
'Mori, Shigeki'
'Okujima, Tetsuo'
'Uno, Hidemitsu'
_publ_section_title
;
 Synthesis, structure and properties of ethyl
 naphth[2,3-f]isoindole-1-carboxylate
;
_journal_issue                   9
_journal_name_full               'RSC Advances'
_journal_page_first              3006
_journal_paper_doi               10.1039/c2ra22870j
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C17 H20 O3 S'
_chemical_formula_sum            'C17 H20 O3 S'
_chemical_formula_weight         304.40
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 122.027(6)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   32.099(6)
_cell_length_b                   6.2507(5)
_cell_length_c                   18.637(3)
_cell_measurement_reflns_used    4614
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.33
_cell_volume                     3170.2(8)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 14.6199
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Mercury-8'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11735
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1296.00
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.410
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0468P)²+1.7522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                3172
_reflns_number_total             3619
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c2ra22870j.txt
_cod_data_source_block           '_BCHDSulfone'
_cod_database_code               7238806
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_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
S1 S 0.110452(12) 0.19111(5) 0.61666(2) 0.02572(12) Uani 1 1 d .
O1 O 0.14868(4) 0.54063(19) 0.47187(6) 0.0372(3) Uani 1 1 d .
O2 O 0.09323(4) 0.33323(18) 0.65608(6) 0.0352(3) Uani 1 1 d .
O3 O 0.12973(4) -0.01479(17) 0.65455(6) 0.0362(3) Uani 1 1 d .
C1 C 0.18486(5) 0.2315(2) 0.57429(9) 0.0274(3) Uani 1 1 d .
H1 H 0.1707(5) 0.107(2) 0.5356(9) 0.028(4) Uiso 1 1 d .
C2 C 0.15507(5) 0.3252(2) 0.60892(8) 0.0246(3) Uani 1 1 d .
C3 C 0.17125(5) 0.5224(2) 0.63744(8) 0.0281(3) Uani 1 1 d .
H3 H 0.1605(6) 0.617(3) 0.6642(11) 0.038(4) Uiso 1 1 d .
C4 C 0.21291(5) 0.5646(2) 0.62272(9) 0.0324(3) Uani 1 1 d .
H4 H 0.2224(6) 0.713(3) 0.6251(10) 0.039(5) Uiso 1 1 d .
C5 C 0.25433(5) 0.4076(3) 0.67742(9) 0.0342(3) Uani 1 1 d .
H5 H 0.2861(6) 0.448(3) 0.7230(10) 0.037(4) Uiso 1 1 d .
C6 C 0.23800(5) 0.2117(2) 0.64920(9) 0.0308(3) Uani 1 1 d .
H6 H 0.2561(6) 0.072(3) 0.6718(10) 0.041(5) Uiso 1 1 d .
C7 C 0.19177(5) 0.4456(2) 0.53690(9) 0.0308(3) Uani 1 1 d .
H7 H 0.2168(6) 0.426(2) 0.5218(9) 0.029(4) Uiso 1 1 d .
C8 C 0.06208(5) 0.1492(2) 0.51089(8) 0.0248(3) Uani 1 1 d .
C9 C 0.05482(5) -0.0505(2) 0.47457(10) 0.0352(3) Uani 1 1 d .
H9 H 0.0756(4) -0.160(2) 0.5038(6) 0.042 Uiso 1 1 calc R
C10 C 0.01521(6) -0.0811(3) 0.39271(11) 0.0425(4) Uani 1 1 d .
H10 H 0.00952(13) -0.221(3) 0.3666(5) 0.051 Uiso 1 1 calc R
C11 C -0.01605(5) 0.0853(3) 0.34843(10) 0.0386(4) Uani 1 1 d .
H11 H -0.0437(5) 0.0622(5) 0.2912(11) 0.046 Uiso 1 1 calc R
C12 C -0.00825(6) 0.2853(3) 0.38511(10) 0.0426(4) Uani 1 1 d .
H12 H -0.0296(4) 0.399(2) 0.3546(6) 0.051 Uiso 1 1 calc R
C13 C 0.03106(6) 0.3182(2) 0.46677(10) 0.0359(3) Uani 1 1 d .
H13 H 0.03670(12) 0.455(3) 0.4923(5) 0.043 Uiso 1 1 calc R
C14 C 0.14061(5) 0.5402(2) 0.38717(9) 0.0326(3) Uani 1 1 d .
C15 C 0.08969(6) 0.6382(3) 0.33374(10) 0.0435(4) Uani 1 1 d .
H15A H 0.0656(3) 0.5459(14) 0.3359(6) 0.065 Uiso 1 1 calc R
H15B H 0.0811(2) 0.6513(19) 0.2748(7) 0.065 Uiso 1 1 calc R
H15C H 0.08950(13) 0.7806(18) 0.3559(5) 0.065 Uiso 1 1 calc R
C16 C 0.14102(7) 0.3144(3) 0.35815(11) 0.0454(4) Uani 1 1 d .
H16A H 0.1733(4) 0.2537(10) 0.3935(6) 0.068 Uiso 1 1 calc R
H16B H 0.1326(5) 0.3171(3) 0.3003(7) 0.068 Uiso 1 1 calc R
H16C H 0.1174(4) 0.2289(12) 0.3622(8) 0.068 Uiso 1 1 calc R
C17 C 0.17887(7) 0.6806(3) 0.38571(11) 0.0436(4) Uani 1 1 d .
H17A H 0.1787(3) 0.8257(17) 0.4081(8) 0.065 Uiso 1 1 calc R
H17B H 0.1709(3) 0.6937(17) 0.3263(7) 0.065 Uiso 1 1 calc R
H17C H 0.2121(4) 0.6147(13) 0.4218(7) 0.065 Uiso 1 1 calc R
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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, 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
O2 S1 O3 118.91(7)
O2 S1 C2 107.65(7)
O3 S1 C2 108.32(6)
O2 S1 C8 108.26(6)
O3 S1 C8 108.04(6)
C2 S1 C8 104.80(6)
C7 O1 C14 117.63(11)
C2 C1 C6 106.86(11)
C2 C1 C7 97.33(11)
C6 C1 C7 97.00(11)
C2 C1 H1 117.4(9)
C6 C1 H1 117.2(9)
C7 C1 H1 117.6(9)
C3 C2 C1 108.93(12)
C3 C2 S1 125.37(11)
C1 C2 S1 125.56(10)
C2 C3 C4 106.35(13)
C2 C3 H3 127.7(10)
C4 C3 H3 125.8(10)
C3 C4 C5 107.77(12)
C3 C4 C7 99.00(11)
C5 C4 C7 97.46(12)
C3 C4 H4 116.1(10)
C5 C4 H4 116.3(10)
C7 C4 H4 117.4(10)
C6 C5 C4 107.91(13)
C6 C5 H5 127.5(10)
C4 C5 H5 124.6(10)
C5 C6 C1 107.56(13)
C5 C6 H6 128.0(10)
C1 C6 H6 124.5(10)
O1 C7 C4 112.31(12)
O1 C7 C1 115.89(12)
C4 C7 C1 92.19(11)
O1 C7 H7 112.7(9)
C4 C7 H7 112.0(9)
C1 C7 H7 110.1(9)
C9 C8 C13 121.19(13)
C9 C8 S1 120.10(11)
C13 C8 S1 118.68(11)
C8 C9 C10 118.82(14)
C8 C9 H9 120.6
C10 C9 H9 120.6
C11 C10 C9 120.51(15)
C11 C10 H10 119.7
C9 C10 H10 119.7
C10 C11 C12 120.26(14)
C10 C11 H11 119.9
C12 C11 H11 119.9
C11 C12 C13 119.89(15)
C11 C12 H12 120.1
C13 C12 H12 120.1
C12 C13 C8 119.33(14)
C12 C13 H13 120.3
C8 C13 H13 120.3
O1 C14 C16 110.99(13)
O1 C14 C15 102.74(11)
C16 C14 C15 110.57(14)
O1 C14 C17 109.68(12)
C16 C14 C17 111.79(13)
C15 C14 C17 110.72(14)
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C14 C16 H16A 109.5
C14 C16 H16B 109.5
H16A C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C14 C17 H17A 109.5
C14 C17 H17B 109.5
H17A C17 H17B 109.5
C14 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4371(10)
S1 O3 1.4403(10)
S1 C2 1.7303(14)
S1 C8 1.7660(13)
O1 C7 1.3987(17)
O1 C14 1.4578(16)
C1 C2 1.5260(18)
C1 C6 1.5323(19)
C1 C7 1.578(2)
C1 H1 0.995(15)
C2 C3 1.3341(19)
C3 C4 1.524(2)
C3 H3 0.947(17)
C4 C5 1.527(2)
C4 C7 1.556(2)
C4 H4 0.972(18)
C5 C6 1.326(2)
C5 H5 0.952(17)
C6 H6 1.009(18)
C7 H7 0.988(16)
C8 C9 1.3799(19)
C8 C13 1.3835(19)
C9 C10 1.387(2)
C9 H9 0.9088
C10 C11 1.375(2)
C10 H10 0.9676
C11 C12 1.383(2)
C11 H11 0.9703
C12 C13 1.383(2)
C12 H12 0.9395
C13 H13 0.9490
C14 C16 1.514(2)
C14 C15 1.520(2)
C14 C17 1.522(2)
C15 H15A 0.9831
C15 H15B 0.9831
C15 H15C 0.9831
C16 H16A 0.9629
C16 H16B 0.9629
C16 H16C 0.9629
C17 H17A 0.9989
C17 H17B 0.9989
C17 H17C 0.9989
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
C6 C1 C2 C3 64.31(14)
C7 C1 C2 C3 -35.32(13)
C6 C1 C2 S1 -111.61(12)
C7 C1 C2 S1 148.76(10)
O2 S1 C2 C3 2.08(14)
O3 S1 C2 C3 -127.69(12)
C8 S1 C2 C3 117.17(12)
O2 S1 C2 C1 177.35(11)
O3 S1 C2 C1 47.58(13)
C8 S1 C2 C1 -67.56(12)
C1 C2 C3 C4 -0.32(14)
S1 C2 C3 C4 175.61(10)
C2 C3 C4 C5 -64.28(15)
C2 C3 C4 C7 36.60(14)
C3 C4 C5 C6 65.04(16)
C7 C4 C5 C6 -36.95(15)
C4 C5 C6 C1 0.06(16)
C2 C1 C6 C5 -63.66(15)
C7 C1 C6 C5 36.21(14)
C14 O1 C7 C4 144.61(13)
C14 O1 C7 C1 -111.21(14)
C3 C4 C7 O1 64.81(14)
C5 C4 C7 O1 174.22(12)
C3 C4 C7 C1 -54.41(12)
C5 C4 C7 C1 55.00(12)
C2 C1 C7 O1 -62.95(14)
C6 C1 C7 O1 -171.03(12)
C2 C1 C7 C4 53.21(11)
C6 C1 C7 C4 -54.87(11)
O2 S1 C8 C9 -141.43(12)
O3 S1 C8 C9 -11.43(14)
C2 S1 C8 C9 103.90(13)
O2 S1 C8 C13 36.59(13)
O3 S1 C8 C13 166.59(12)
C2 S1 C8 C13 -78.08(13)
C13 C8 C9 C10 -0.9(2)
S1 C8 C9 C10 177.10(12)
C8 C9 C10 C11 0.4(2)
C9 C10 C11 C12 0.1(3)
C10 C11 C12 C13 -0.2(3)
C11 C12 C13 C8 -0.2(3)
C9 C8 C13 C12 0.8(2)
S1 C8 C13 C12 -177.23(13)
C7 O1 C14 C16 57.51(17)
C7 O1 C14 C15 175.71(13)
C7 O1 C14 C17 -66.50(17)
