#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:29:08 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178480 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/01/4030172.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_4030172
loop_
_publ_author_name
'Chen, Zhi-Wei'
'Zhu, Yi-Zhou'
'Ou, Jin-Wang'
'Wang, Ya-Ping'
'Zheng, Jian-Yu'
_publ_section_title
;
 Metal-free iodine(III)-promoted synthesis of isoquinolones.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10988
_journal_page_last               10998
_journal_paper_doi               10.1021/jo5020307
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C17 H13 N O3'
_chemical_formula_weight         279.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 102.12(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4145(17)
_cell_length_b                   8.9482(18)
_cell_length_c                   17.838(4)
_cell_measurement_reflns_used    3422
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9344
_cell_measurement_theta_min      2.4757
_cell_volume                     1313.2(5)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13022
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.044(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0888P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1388
_reflns_number_gt                2476
_reflns_number_total             3137
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5020307_si_004.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4030170--4030173.cif.
;
_cod_original_cell_volume        1313.1(5)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4030172
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O -0.03598(13) 0.07037(12) 1.15856(6) 0.0250(3) Uani 1 1 d .
O2 O -0.25692(12) 0.05355(11) 1.03053(6) 0.0222(3) Uani 1 1 d .
O3 O -0.35649(13) 0.16645(13) 0.88640(6) 0.0315(3) Uani 1 1 d .
N1 N -0.11615(14) 0.13691(13) 1.03293(6) 0.0180(3) Uani 1 1 d .
C1 C -0.00606(17) 0.13558(15) 1.10267(8) 0.0186(3) Uani 1 1 d .
C2 C 0.14141(17) 0.22288(15) 1.10290(8) 0.0176(3) Uani 1 1 d .
C3 C 0.25200(18) 0.24297(17) 1.17294(8) 0.0220(3) Uani 1 1 d .
H3 H 0.2358 0.1919 1.2174 0.026 Uiso 1 1 calc R
C4 C 0.38376(18) 0.33620(18) 1.17757(8) 0.0263(4) Uani 1 1 d .
H4 H 0.4585 0.3495 1.2250 0.032 Uiso 1 1 calc R
C5 C 0.40680(18) 0.41144(18) 1.11173(9) 0.0265(4) Uani 1 1 d .
H5 H 0.4950 0.4792 1.1152 0.032 Uiso 1 1 calc R
C6 C 0.30279(17) 0.38810(17) 1.04197(8) 0.0214(3) Uani 1 1 d .
H6 H 0.3219 0.4379 0.9977 0.026 Uiso 1 1 calc R
C7 C 0.16866(16) 0.29143(16) 1.03556(7) 0.0175(3) Uani 1 1 d .
C8 C 0.05478(16) 0.26603(15) 0.96327(7) 0.0159(3) Uani 1 1 d .
C9 C -0.08674(16) 0.19281(15) 0.96412(7) 0.0163(3) Uani 1 1 d .
C10 C 0.09407(17) 0.32701(15) 0.89141(7) 0.0167(3) Uani 1 1 d .
C11 C 0.23252(17) 0.27636(16) 0.86723(7) 0.0188(3) Uani 1 1 d .
H11 H 0.2973 0.1993 0.8948 0.023 Uiso 1 1 calc R
C12 C 0.27541(17) 0.33860(16) 0.80296(8) 0.0211(3) Uani 1 1 d .
H12 H 0.3692 0.3034 0.7867 0.025 Uiso 1 1 calc R
C13 C 0.18224(18) 0.45179(16) 0.76239(8) 0.0221(3) Uani 1 1 d .
H13 H 0.2130 0.4950 0.7189 0.026 Uiso 1 1 calc R
C14 C 0.04378(18) 0.50161(16) 0.78566(8) 0.0228(3) Uani 1 1 d .
H14 H -0.0208 0.5784 0.7578 0.027 Uiso 1 1 calc R
C15 C -0.00048(17) 0.43905(15) 0.84988(8) 0.0200(3) Uani 1 1 d .
H15 H -0.0956 0.4730 0.8654 0.024 Uiso 1 1 calc R
C16 C -0.21121(17) 0.17354(15) 0.89178(8) 0.0198(3) Uani 1 1 d .
H16 H -0.1726 0.1661 0.8456 0.024 Uiso 1 1 calc R
C17 C -0.37625(18) 0.14609(18) 1.05579(9) 0.0283(4) Uani 1 1 d .
H17A H -0.3288 0.1888 1.1061 0.043 Uiso 1 1 calc R
H17B H -0.4711 0.0853 1.0596 0.043 Uiso 1 1 calc R
H17C H -0.4098 0.2269 1.0188 0.043 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 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
N1 O2 C17 109.01(10)
C1 N1 O2 115.26(10)
C1 N1 C9 125.74(12)
O2 N1 C9 118.16(11)
O1 C1 N1 121.41(13)
O1 C1 C2 124.73(13)
N1 C1 C2 113.82(11)
C3 C2 C7 120.43(13)
C3 C2 C1 118.26(12)
C7 C2 C1 121.24(13)
C4 C3 C2 120.41(13)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C5 119.49(14)
C3 C4 H4 120.3
C5 C4 H4 120.3
C6 C5 C4 120.67(14)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C7 120.84(13)
C5 C6 H6 119.6
C7 C6 H6 119.6
C6 C7 C2 117.99(13)
C6 C7 C8 122.41(12)
C2 C7 C8 119.53(13)
C9 C8 C7 118.70(12)
C9 C8 C10 122.49(12)
C7 C8 C10 118.75(12)
C8 C9 N1 119.96(12)
C8 C9 C16 120.19(12)
N1 C9 C16 119.85(12)
C15 C10 C11 119.25(13)
C15 C10 C8 121.01(12)
C11 C10 C8 119.66(12)
C12 C11 C10 120.12(13)
C12 C11 H11 119.9
C10 C11 H11 119.9
C13 C12 C11 120.46(13)
C13 C12 H12 119.8
C11 C12 H12 119.8
C12 C13 C14 119.71(13)
C12 C13 H13 120.1
C14 C13 H13 120.1
C13 C14 C15 120.13(13)
C13 C14 H14 119.9
C15 C14 H14 119.9
C10 C15 C14 120.32(13)
C10 C15 H15 119.8
C14 C15 H15 119.8
O3 C16 C9 126.17(13)
O3 C16 H16 116.9
C9 C16 H16 116.9
O2 C17 H17A 109.5
O2 C17 H17B 109.5
H17A C17 H17B 109.5
O2 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
O1 C1 1.2259(17)
O2 N1 1.3928(14)
O2 C17 1.4446(17)
O3 C16 1.2076(17)
N1 C1 1.3864(18)
N1 C9 1.3948(17)
C1 C2 1.466(2)
C2 C3 1.404(2)
C2 C7 1.4097(19)
C3 C4 1.376(2)
C3 H3 0.9500
C4 C5 1.402(2)
C4 H4 0.9500
C5 C6 1.379(2)
C5 H5 0.9500
C6 C7 1.407(2)
C6 H6 0.9500
C7 C8 1.4539(19)
C8 C9 1.3620(19)
C8 C10 1.4928(18)
C9 C16 1.4915(19)
C10 C15 1.3926(19)
C10 C11 1.3999(19)
C11 C12 1.3886(19)
C11 H11 0.9500
C12 C13 1.388(2)
C12 H12 0.9500
C13 C14 1.390(2)
C13 H13 0.9500
C14 C15 1.3940(19)
C14 H14 0.9500
C15 H15 0.9500
C16 H16 0.9500
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
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
C17 O2 N1 C1 87.55(13)
C17 O2 N1 C9 -102.36(13)
O2 N1 C1 O1 -3.07(18)
C9 N1 C1 O1 -172.30(12)
O2 N1 C1 C2 179.30(10)
C9 N1 C1 C2 10.07(19)
O1 C1 C2 C3 -4.7(2)
N1 C1 C2 C3 172.79(12)
O1 C1 C2 C7 178.33(13)
N1 C1 C2 C7 -4.13(19)
C7 C2 C3 C4 3.5(2)
C1 C2 C3 C4 -173.46(13)
C2 C3 C4 C5 0.1(2)
C3 C4 C5 C6 -2.7(2)
C4 C5 C6 C7 1.7(2)
C5 C6 C7 C2 1.8(2)
C5 C6 C7 C8 178.91(13)
C3 C2 C7 C6 -4.4(2)
C1 C2 C7 C6 172.45(12)
C3 C2 C7 C8 178.42(12)
C1 C2 C7 C8 -4.72(19)
C6 C7 C8 C9 -168.40(13)
C2 C7 C8 C9 8.64(19)
C6 C7 C8 C10 8.94(19)
C2 C7 C8 C10 -174.01(12)
C7 C8 C9 N1 -3.40(19)
C10 C8 C9 N1 179.36(11)
C7 C8 C9 C16 175.99(11)
C10 C8 C9 C16 -1.3(2)
C1 N1 C9 C8 -6.5(2)
O2 N1 C9 C8 -175.49(11)
C1 N1 C9 C16 174.07(13)
O2 N1 C9 C16 5.12(17)
C9 C8 C10 C15 63.04(19)
C7 C8 C10 C15 -114.20(15)
C9 C8 C10 C11 -120.13(15)
C7 C8 C10 C11 62.63(17)
C15 C10 C11 C12 0.6(2)
C8 C10 C11 C12 -176.24(12)
C10 C11 C12 C13 0.3(2)
C11 C12 C13 C14 -0.9(2)
C12 C13 C14 C15 0.6(2)
C11 C10 C15 C14 -1.0(2)
C8 C10 C15 C14 175.84(13)
C13 C14 C15 C10 0.4(2)
C8 C9 C16 O3 -149.37(15)
N1 C9 C16 O3 30.0(2)
