#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/51/4025109.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_4025109
loop_
_publ_author_name
'Kanniyappan Parthasarathy'
'Chien-Hong Cheng'
_publ_section_title
;
Easy Access to Isoquinolines and Tetrahydroquinolines from Ketoximes and
Alkynes via Rhodium-Catalyzed C-H Bond Activation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9359
_journal_page_last               9364
_journal_paper_doi               10.1021/jo902084j
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C17 H17 N O'
_chemical_formula_weight         251.32
_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                 93.255(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2926(13)
_cell_length_b                   10.0449(17)
_cell_length_c                   17.180(3)
_cell_measurement_reflns_used    3099
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     1428.8(4)
_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  'Shelxtl-97 (Sheldrick, 2008)'
_computing_structure_solution    'Shelxtl-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10322
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5423
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       Lump
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0516
_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)+(0.0728P)²+0.2113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1531
_reflns_number_gt                2667
_reflns_number_total             3549
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902084j_si_002.cif
_cod_data_source_block           08dc442m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4025109
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.02024(18) 0.94077(15) 0.34932(8) 0.0536(3) Uani 1 1 d . . .
C2 C -0.0908(2) 0.8245(2) 0.37391(11) 0.0729(5) Uani 1 1 d . . .
H2 H -0.0585 0.7430 0.3544 0.087 Uiso 1 1 calc R . .
C3 C -0.2093(2) 0.8290(3) 0.42752(13) 0.0959(7) Uani 1 1 d . . .
H3 H -0.2565 0.7506 0.4439 0.115 Uiso 1 1 calc R . .
C4 C -0.2573(3) 0.9501(3) 0.45662(12) 0.1010(9) Uani 1 1 d . . .
H4 H -0.3357 0.9530 0.4932 0.121 Uiso 1 1 calc R . .
C5 C -0.1903(2) 1.0650(3) 0.43189(12) 0.0875(6) Uani 1 1 d . . .
H5 H -0.2229 1.1463 0.4516 0.105 Uiso 1 1 calc R . .
C6 C -0.0746(2) 1.06112(18) 0.37801(10) 0.0673(4) Uani 1 1 d . . .
H6 H -0.0318 1.1404 0.3603 0.081 Uiso 1 1 calc R . .
C7 C 0.10710(17) 0.94282(14) 0.29245(8) 0.0510(3) Uani 1 1 d . . .
H7 H 0.0934 1.0042 0.2521 0.061 Uiso 1 1 calc R . .
C8 C 0.23911(17) 0.86730(14) 0.29203(7) 0.0511(3) Uani 1 1 d . . .
C9 C 0.35580(16) 0.88691(14) 0.22994(8) 0.0488(3) Uani 1 1 d . . .
C10 C 0.30888(15) 0.88392(13) 0.15007(7) 0.0453(3) Uani 1 1 d . . .
C11 C 0.42306(17) 0.91178(16) 0.09574(9) 0.0559(4) Uani 1 1 d . . .
H11 H 0.3920 0.9106 0.0429 0.067 Uiso 1 1 calc R . .
C12 C 0.58108(19) 0.94097(18) 0.11884(11) 0.0675(4) Uani 1 1 d . . .
H12 H 0.6553 0.9602 0.0819 0.081 Uiso 1 1 calc R . .
C13 C 0.62810(19) 0.94141(19) 0.19673(12) 0.0717(5) Uani 1 1 d . . .
H13 H 0.7348 0.9598 0.2126 0.086 Uiso 1 1 calc R . .
C14 C 0.51721(19) 0.91461(17) 0.25132(10) 0.0638(4) Uani 1 1 d . . .
H14 H 0.5508 0.9150 0.3039 0.077 Uiso 1 1 calc R . .
C15 C 0.2854(2) 0.7661(2) 0.35415(10) 0.0784(5) Uani 1 1 d . . .
H15A H 0.2253 0.7825 0.3993 0.118 Uiso 1 1 calc R . .
H15B H 0.3988 0.7731 0.3680 0.118 Uiso 1 1 calc R . .
H15C H 0.2615 0.6783 0.3347 0.118 Uiso 1 1 calc R . .
C16 C 0.14410(15) 0.84310(14) 0.11998(7) 0.0460(3) Uani 1 1 d . . .
C17 C 0.0674(2) 0.71902(16) 0.14869(9) 0.0624(4) Uani 1 1 d . . .
H17A H -0.0348 0.7406 0.1691 0.094 Uiso 1 1 calc R . .
H17B H 0.1366 0.6796 0.1890 0.094 Uiso 1 1 calc R . .
H17C H 0.0510 0.6572 0.1064 0.094 Uiso 1 1 calc R . .
N1 N 0.08154(13) 0.91418(12) 0.06444(6) 0.0508(3) Uani 1 1 d . . .
O1 O -0.06619(12) 0.86112(12) 0.03327(6) 0.0654(3) Uani 1 1 d . . .
H1 H -0.1035 0.9100 -0.0015 0.098 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.34(15) . . ?
C2 C1 C7 122.94(14) . . ?
C6 C1 C7 118.70(14) . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.18(18) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 121.15(19) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C8 C7 C1 127.84(13) . . ?
C8 C7 H7 116.1 . . ?
C1 C7 H7 116.1 . . ?
C7 C8 C9 119.65(12) . . ?
C7 C8 C15 123.80(14) . . ?
C9 C8 C15 116.45(12) . . ?
C14 C9 C10 118.00(13) . . ?
C14 C9 C8 119.27(12) . . ?
C10 C9 C8 122.68(12) . . ?
C11 C10 C9 119.22(12) . . ?
C11 C10 C16 117.83(12) . . ?
C9 C10 C16 122.82(12) . . ?
C12 C11 C10 121.33(14) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 119.61(15) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 119.99(14) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 121.83(14) . . ?
C13 C14 H14 119.1 . . ?
C9 C14 H14 119.1 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C10 115.49(12) . . ?
N1 C16 C17 123.34(12) . . ?
C10 C16 C17 120.91(12) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 N1 O1 112.25(11) . . ?
N1 O1 H1 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(2) . ?
C1 C6 1.390(2) . ?
C1 C7 1.479(2) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.332(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.493(2) . ?
C8 C15 1.508(2) . ?
C9 C14 1.396(2) . ?
C9 C10 1.4052(18) . ?
C10 C11 1.3952(19) . ?
C10 C16 1.4907(18) . ?
C11 C12 1.379(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N1 1.2780(17) . ?
C16 C17 1.496(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 O1 1.4132(14) . ?
O1 H1 0.8200 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659100
