#------------------------------------------------------------------------------
#$Date: 2019-11-28 18:59:52 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244366 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/88/7238807.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_7238807
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         'C16 H21 N O3'
_chemical_formula_sum            'C16 H21 N O3'
_chemical_formula_weight         275.35
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.300(6)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.651(4)
_cell_length_b                   9.558(4)
_cell_length_c                   17.186(7)
_cell_measurement_reflns_used    5154
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.02
_cell_measurement_theta_min      2.36
_cell_volume                     1417.0(11)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_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    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      120(0)
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22439
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             592.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0466P)²+0.6124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                3139
_reflns_number_total             3266
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c2ra22870j.txt
_cod_data_source_block           BCODpyrroleOtBu
_cod_original_cell_volume        1417.1(10)
_cod_database_code               7238807
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_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
O1 O 0.32668(8) 0.82208(8) 0.48254(4) 0.01384(17) Uani 1 1 d .
O2 O 0.64465(9) 0.65529(8) 0.70694(4) 0.01839(18) Uani 1 1 d .
O3 O 0.71884(10) 0.43524(9) 0.67906(5) 0.0250(2) Uani 1 1 d .
N1 N 0.45399(11) 0.40982(10) 0.57240(5) 0.0160(2) Uani 1 1 d .
H1 H 0.5236(18) 0.3435(17) 0.5642(9) 0.028(4) Uiso 1 1 d .
C1 C 0.48730(12) 0.52778(11) 0.61770(6) 0.0146(2) Uani 1 1 d .
C2 C 0.31576(12) 0.42806(11) 0.52919(6) 0.0157(2) Uani 1 1 d .
H2 H 0.2792(16) 0.3556(15) 0.4933(8) 0.021(3) Uiso 1 1 d .
C3 C 0.25946(12) 0.55749(11) 0.54725(6) 0.0140(2) Uani 1 1 d .
C4 C 0.12539(12) 0.65830(11) 0.53320(6) 0.0145(2) Uani 1 1 d .
H4 H 0.0540(16) 0.6464(14) 0.4859(8) 0.017(3) Uiso 1 1 d .
C5 C 0.04975(13) 0.67147(12) 0.61089(6) 0.0180(2) Uani 1 1 d .
H5 H -0.0543(18) 0.6361(16) 0.6199(8) 0.027(4) Uiso 1 1 d .
C6 C 0.15135(13) 0.73180(12) 0.66259(6) 0.0176(2) Uani 1 1 d .
H6 H 0.1382(16) 0.7519(16) 0.7174(9) 0.025(4) Uiso 1 1 d .
C7 C 0.30083(12) 0.76168(11) 0.62241(6) 0.0142(2) Uani 1 1 d .
H7 H 0.3707(16) 0.8308(14) 0.6477(8) 0.016(3) Uiso 1 1 d .
C8 C 0.36677(12) 0.62047(11) 0.60225(6) 0.0133(2) Uani 1 1 d .
C9 C 0.22028(12) 0.79933(11) 0.54018(6) 0.0138(2) Uani 1 1 d .
H9 H 0.1505(16) 0.8810(15) 0.5446(8) 0.017 Uiso 1 1 d xyz
C10 C 0.62760(12) 0.53130(11) 0.66982(6) 0.0158(2) Uani 1 1 d .
C11 C 0.77201(13) 0.66365(12) 0.76689(6) 0.0183(2) Uani 1 1 d .
H11A H 0.8638(17) 0.6170(16) 0.7480(8) 0.025(3) Uiso 1 1 d .
H11B H 0.7384(17) 0.6127(16) 0.8129(9) 0.025(3) Uiso 1 1 d .
C12 C 0.80041(14) 0.81596(13) 0.78386(7) 0.0232(3) Uani 1 1 d .
H12A H 0.838(2) 0.8645(18) 0.7370(10) 0.037(3) Uiso 1 1 d .
H12B H 0.879(2) 0.8262(17) 0.8289(10) 0.037(3) Uiso 1 1 d .
H12C H 0.707(2) 0.8619(18) 0.7980(10) 0.037(3) Uiso 1 1 d .
C13 C 0.27836(12) 0.92229(11) 0.42104(6) 0.0141(2) Uani 1 1 d .
C14 C 0.27915(14) 1.07048(12) 0.45421(7) 0.0185(2) Uani 1 1 d .
H14A H 0.2009(18) 1.0838(16) 0.4948(9) 0.029(2) Uiso 1 1 d .
H14B H 0.2473(18) 1.1380(17) 0.4115(9) 0.029(2) Uiso 1 1 d .
H14C H 0.3839(18) 1.0953(17) 0.4776(9) 0.029(2) Uiso 1 1 d .
C15 C 0.11935(13) 0.88258(12) 0.38294(6) 0.0180(2) Uani 1 1 d .
H15A H 0.1219(17) 0.7849(17) 0.3638(8) 0.026(2) Uiso 1 1 d .
H15B H 0.0956(17) 0.9444(16) 0.3379(9) 0.026(2) Uiso 1 1 d .
H15C H 0.0350(17) 0.8937(16) 0.4196(9) 0.026(2) Uiso 1 1 d .
C16 C 0.40124(13) 0.90880(12) 0.36232(6) 0.0182(2) Uani 1 1 d .
H16A H 0.5082(18) 0.9244(16) 0.3886(9) 0.026(2) Uiso 1 1 d .
H16B H 0.3817(17) 0.9802(16) 0.3214(9) 0.026(2) Uiso 1 1 d .
H16C H 0.3984(17) 0.8155(16) 0.3369(9) 0.026(2) Uiso 1 1 d .
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)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 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)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 O1 C13 116.06(8)
C10 O2 C11 115.72(8)
C2 N1 C1 109.67(9)
C2 N1 H1 125.2(10)
C1 N1 H1 123.5(10)
C8 C1 N1 106.96(9)
C8 C1 C10 133.48(10)
N1 C1 C10 119.54(9)
N1 C2 C3 107.57(9)
N1 C2 H2 119.1(9)
C3 C2 H2 133.3(9)
C2 C3 C8 108.02(9)
C2 C3 C4 144.88(10)
C8 C3 C4 107.07(9)
C3 C4 C5 106.56(8)
C3 C4 C9 98.26(8)
C5 C4 C9 96.72(8)
C3 C4 H4 118.8(8)
C5 C4 H4 116.3(8)
C9 C4 H4 116.7(8)
C6 C5 C4 108.20(10)
C6 C5 H5 127.5(9)
C4 C5 H5 124.2(9)
C5 C6 C7 108.40(10)
C5 C6 H6 127.5(9)
C7 C6 H6 124.0(9)
C8 C7 C6 106.31(9)
C8 C7 C9 98.49(8)
C6 C7 C9 96.63(8)
C8 C7 H7 118.3(8)
C6 C7 H7 116.1(8)
C9 C7 H7 117.6(8)
C1 C8 C3 107.78(10)
C1 C8 C7 145.13(10)
C3 C8 C7 107.06(9)
O1 C9 C7 113.34(8)
O1 C9 C4 116.04(8)
C7 C9 C4 93.77(8)
O1 C9 H9 111.2(8)
C7 C9 H9 110.1(8)
C4 C9 H9 111.2(8)
O3 C10 O2 123.77(10)
O3 C10 C1 124.61(10)
O2 C10 C1 111.62(9)
O2 C11 C12 107.18(9)
O2 C11 H11A 109.1(9)
C12 C11 H11A 112.2(9)
O2 C11 H11B 106.7(9)
C12 C11 H11B 112.0(9)
H11A C11 H11B 109.4(12)
C11 C12 H12A 110.5(10)
C11 C12 H12B 109.8(10)
H12A C12 H12B 109.4(14)
C11 C12 H12C 111.3(10)
H12A C12 H12C 108.7(14)
H12B C12 H12C 107.1(14)
O1 C13 C16 104.30(8)
O1 C13 C15 110.26(8)
C16 C13 C15 110.22(9)
O1 C13 C14 110.15(9)
C16 C13 C14 109.98(9)
C15 C13 C14 111.69(9)
C13 C14 H14A 112.9(9)
C13 C14 H14B 109.4(9)
H14A C14 H14B 105.1(12)
C13 C14 H14C 110.6(9)
H14A C14 H14C 109.1(12)
H14B C14 H14C 109.6(13)
C13 C15 H15A 109.6(9)
C13 C15 H15B 108.5(9)
H15A C15 H15B 108.3(12)
C13 C15 H15C 112.2(8)
H15A C15 H15C 110.1(12)
H15B C15 H15C 108.2(12)
C13 C16 H16A 110.6(8)
C13 C16 H16B 108.9(9)
H16A C16 H16B 108.6(12)
C13 C16 H16C 111.8(9)
H16A C16 H16C 108.8(12)
H16B C16 H16C 108.1(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.4185(13)
O1 C13 1.4640(12)
O2 C10 1.3488(14)
O2 C11 1.4531(13)
O3 C10 1.2135(14)
N1 C2 1.3706(14)
N1 C1 1.3881(14)
N1 H1 0.893(16)
C1 C8 1.3788(15)
C1 C10 1.4538(15)
C2 C3 1.3736(16)
C2 H2 0.965(15)
C3 C8 1.4093(15)
C3 C4 1.5132(15)
C4 C5 1.5355(15)
C4 C9 1.5782(15)
C4 H4 0.990(14)
C5 C6 1.3332(17)
C5 H5 0.984(15)
C6 C7 1.5377(15)
C6 H6 0.977(14)
C7 C8 1.5156(15)
C7 C9 1.5699(15)
C7 H7 0.975(14)
C9 H9 0.993(14)
C11 C12 1.5014(18)
C11 H11A 0.987(15)
C11 H11B 0.990(15)
C12 H12A 1.006(17)
C12 H12B 0.996(17)
C12 H12C 0.964(17)
C13 C16 1.5251(15)
C13 C15 1.5264(15)
C13 C14 1.5266(15)
C14 H14A 1.016(16)
C14 H14B 1.000(16)
C14 H14C 0.992(16)
C15 H15A 0.991(16)
C15 H15B 0.984(15)
C15 H15C 1.005(15)
C16 H16A 1.010(15)
C16 H16B 0.986(16)
C16 H16C 0.992(15)
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
C2 N1 C1 C8 0.19(11)
C2 N1 C1 C10 178.80(9)
C1 N1 C2 C3 -0.50(12)
N1 C2 C3 C8 0.62(12)
N1 C2 C3 C4 -176.87(14)
C2 C3 C4 C5 113.36(16)
C8 C3 C4 C5 -64.14(11)
C2 C3 C4 C9 -147.05(15)
C8 C3 C4 C9 35.45(10)
C3 C4 C5 C6 65.40(12)
C9 C4 C5 C6 -35.32(11)
C4 C5 C6 C7 -0.25(12)
C5 C6 C7 C8 -64.96(11)
C5 C6 C7 C9 35.93(11)
N1 C1 C8 C3 0.20(11)
C10 C1 C8 C3 -178.14(11)
N1 C1 C8 C7 177.57(14)
C10 C1 C8 C7 -0.8(2)
C2 C3 C8 C1 -0.51(12)
C4 C3 C8 C1 177.98(8)
C2 C3 C8 C7 -178.93(8)
C4 C3 C8 C7 -0.44(11)
C6 C7 C8 C1 -112.84(16)
C9 C7 C8 C1 147.65(15)
C6 C7 C8 C3 64.54(10)
C9 C7 C8 C3 -34.97(10)
C13 O1 C9 C7 -149.31(8)
C13 O1 C9 C4 103.80(10)
C8 C7 C9 O1 -66.87(10)
C6 C7 C9 O1 -174.52(8)
C8 C7 C9 C4 53.63(9)
C6 C7 C9 C4 -54.02(8)
C3 C4 C9 O1 64.43(10)
C5 C4 C9 O1 172.31(8)
C3 C4 C9 C7 -53.87(8)
C5 C4 C9 C7 54.01(9)
C11 O2 C10 O3 -6.82(15)
C11 O2 C10 C1 173.29(8)
C8 C1 C10 O3 175.89(11)
N1 C1 C10 O3 -2.29(16)
C8 C1 C10 O2 -4.22(17)
N1 C1 C10 O2 177.60(9)
C10 O2 C11 C12 163.72(9)
C9 O1 C13 C16 -171.76(8)
C9 O1 C13 C15 -53.46(11)
C9 O1 C13 C14 70.26(11)
