#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:36:41 +0100 (lun 21 de mar de 2016) $
#$Revision: 178487 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/08/4030892.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_4030892
loop_
_publ_author_name
'Mayo, Muhammad Shareef'
'Yu, Xiaoqiang'
'Feng, Xiujuan'
'Yamamoto, Yoshinori'
'Bao, Ming'
_publ_section_title
;
 Isoquinolone Synthesis through SNAr Reaction of 2-Halobenzonitriles with
 Ketones Followed by Cyclization.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3998
_journal_page_last               4002
_journal_paper_doi               10.1021/acs.joc.5b00357
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C15 H11 N O'
_chemical_formula_sum            'C15 H11 N O'
_chemical_formula_weight         221.25
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.586(14)
_cell_angle_beta                 94.219(19)
_cell_angle_gamma                90.27(2)
_cell_formula_units_Z            2
_cell_length_a                   3.882(5)
_cell_length_b                   12.069(14)
_cell_length_c                   12.451(16)
_cell_measurement_temperature    296(2)
_cell_volume                     557.4(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3206
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle-like
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       0.027(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1549
_refine_ls_R_factor_gt           0.1247
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1469P)²+2.7772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3586
_refine_ls_wR_factor_ref         0.3851
_reflns_number_gt                1302
_reflns_number_total             1895
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00357_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/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 3143 2015-03-26 13:38:13Z robertas 

 Adding full bibliography for 4030892.cif.
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               4030892
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.1749(16) 0.5018(4) 0.3595(4) 0.0488(15) Uani 1 1 d .
H1N H 0.1003 0.5505 0.4174 0.059 Uiso 1 1 calc R
C10 C 0.3633(18) 0.3133(5) 0.2660(5) 0.0482(17) Uani 1 1 d .
C8 C 0.3549(19) 0.4695(5) 0.1760(5) 0.0513(17) Uani 1 1 d .
H8 H 0.3931 0.4958 0.1145 0.062 Uiso 1 1 calc R
C9 C 0.4241(18) 0.3507(5) 0.1725(5) 0.0483(17) Uani 1 1 d .
C6 C -0.021(2) 0.8199(6) 0.2068(7) 0.066(2) Uani 1 1 d .
H6 H -0.1181 0.8439 0.1470 0.079 Uiso 1 1 calc R
C7 C 0.2349(17) 0.5419(5) 0.2688(5) 0.0437(16) Uani 1 1 d .
C4 C 0.1760(17) 0.6676(5) 0.2839(5) 0.0438(15) Uani 1 1 d .
C11 C 0.2240(18) 0.3914(5) 0.3650(5) 0.0462(16) Uani 1 1 d .
C3 C 0.260(2) 0.7492(5) 0.3859(6) 0.0521(18) Uani 1 1 d .
H3 H 0.3524 0.7259 0.4468 0.062 Uiso 1 1 calc R
C2 C 0.206(2) 0.8655(6) 0.3982(7) 0.064(2) Uani 1 1 d .
H2 H 0.2641 0.9198 0.4671 0.076 Uiso 1 1 calc R
C12 C 0.433(2) 0.1977(5) 0.2652(6) 0.058(2) Uani 1 1 d .
H12 H 0.3939 0.1727 0.3274 0.069 Uiso 1 1 calc R
C15 C 0.557(2) 0.2720(6) 0.0779(6) 0.061(2) Uani 1 1 d .
H15 H 0.6008 0.2963 0.0157 0.073 Uiso 1 1 calc R
C14 C 0.620(2) 0.1603(6) 0.0776(7) 0.068(2) Uani 1 1 d .
H14 H 0.7029 0.1089 0.0147 0.081 Uiso 1 1 calc R
C5 C 0.034(2) 0.7036(6) 0.1929(6) 0.0565(19) Uani 1 1 d .
H5 H -0.0234 0.6497 0.1237 0.068 Uiso 1 1 calc R
C13 C 0.559(2) 0.1233(6) 0.1721(7) 0.068(2) Uani 1 1 d .
H13 H 0.6044 0.0475 0.1715 0.081 Uiso 1 1 calc R
C1 C 0.068(2) 0.9005(6) 0.3088(7) 0.064(2) Uani 1 1 d .
H1 H 0.0344 0.9786 0.3170 0.077 Uiso 1 1 calc R
O1 O 0.1605(15) 0.3627(4) 0.4503(4) 0.0604(15) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.069(4) 0.034(3) 0.044(3) 0.012(2) 0.004(3) 0.002(2)
C10 0.055(4) 0.040(3) 0.045(3) 0.007(3) -0.006(3) -0.001(3)
C8 0.064(5) 0.045(4) 0.044(4) 0.012(3) 0.003(3) -0.001(3)
C9 0.053(4) 0.044(3) 0.042(3) 0.005(3) -0.005(3) -0.007(3)
C6 0.081(6) 0.056(4) 0.067(5) 0.030(4) 0.004(4) 0.010(4)
C7 0.051(4) 0.036(3) 0.043(3) 0.012(3) -0.005(3) -0.006(3)
C4 0.044(4) 0.039(3) 0.049(4) 0.014(3) 0.005(3) -0.004(3)
C11 0.057(4) 0.038(3) 0.043(3) 0.012(3) -0.005(3) -0.003(3)
C3 0.065(5) 0.039(3) 0.051(4) 0.012(3) 0.001(3) -0.002(3)
C2 0.078(6) 0.040(4) 0.068(5) 0.007(3) 0.004(4) 0.000(3)
C12 0.071(5) 0.039(3) 0.058(4) 0.010(3) -0.010(4) 0.000(3)
C15 0.071(5) 0.056(4) 0.048(4) 0.002(3) 0.003(3) 0.002(4)
C14 0.081(6) 0.049(4) 0.058(4) -0.005(3) -0.004(4) 0.007(4)
C5 0.066(5) 0.054(4) 0.053(4) 0.022(3) -0.001(3) -0.004(3)
C13 0.086(6) 0.036(4) 0.069(5) 0.000(3) -0.012(4) 0.009(3)
C1 0.067(5) 0.041(4) 0.091(6) 0.030(4) 0.010(4) 0.008(3)
O1 0.092(4) 0.045(3) 0.048(3) 0.019(2) 0.011(2) 0.007(2)
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
C11 N1 C7 125.6(6)
C9 C10 C12 120.0(6)
C9 C10 C11 120.9(6)
C12 C10 C11 119.1(6)
C7 C8 C9 119.9(6)
C10 C9 C15 119.1(6)
C10 C9 C8 118.9(6)
C15 C9 C8 122.0(6)
C1 C6 C5 120.6(7)
C8 C7 N1 119.7(6)
C8 C7 C4 124.1(6)
N1 C7 C4 116.1(6)
C3 C4 C5 119.3(6)
C3 C4 C7 121.2(6)
C5 C4 C7 119.5(6)
O1 C11 N1 121.2(6)
O1 C11 C10 123.8(6)
N1 C11 C10 114.9(5)
C4 C3 C2 120.5(6)
C1 C2 C3 120.1(7)
C13 C12 C10 119.6(7)
C14 C15 C9 120.4(7)
C15 C14 C13 120.2(7)
C6 C5 C4 119.5(7)
C12 C13 C14 120.7(7)
C2 C1 C6 120.1(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C11 1.367(8)
N1 C7 1.382(8)
C10 C9 1.398(9)
C10 C12 1.419(9)
C10 C11 1.463(10)
C8 C7 1.350(9)
C8 C9 1.448(9)
C9 C15 1.417(10)
C6 C1 1.380(11)
C6 C5 1.383(10)
C7 C4 1.495(9)
C4 C3 1.383(9)
C4 C5 1.403(9)
C11 O1 1.247(7)
C3 C2 1.386(9)
C2 C1 1.375(10)
C12 C13 1.371(11)
C15 C14 1.370(10)
C14 C13 1.408(12)
