#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:44:39 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180313 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/27/7152764.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_7152764
loop_
_publ_author_name
'Deponti, Monica'
'Kozhushkov, Sergei I.'
'Yufit, Dmitry S.'
'Ackermann, Lutz'
_publ_section_title
;
 Ruthenium-catalyzed C-H/O-H and C-H/N-H bond functionalizations:
 oxidative annulations of cyclopropyl-substituted alkynes.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              142
_journal_page_last               148
_journal_paper_doi               10.1039/c2ob26250a
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C16 H19 N O'
_chemical_formula_sum            'C16 H19 N O'
_chemical_formula_weight         241.32
_chemical_name_common
4-cyclopropyl-2-methyl-3-(n-propyl)-isoquinolin-1(2H)-one
_chemical_name_systematic
;
4-cyclopropyl-2-methyl-3-(n-propyl)-isoquinolin-1(2H)-one
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-06-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                96.304(2)
_cell_angle_beta                 100.043(2)
_cell_angle_gamma                108.110(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9056(4)
_cell_length_b                   8.8734(5)
_cell_length_c                   9.7298(5)
_cell_measurement_reflns_used    2375
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.98
_cell_measurement_theta_min      2.16
_cell_volume                     628.90(6)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       '/w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10556
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.16
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           10.0
_diffrn_source_power             0.3
_diffrn_source_target            Mo
_diffrn_source_voltage           30.0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0582
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1688
_reflns_number_gt                2073
_reflns_number_total             3344
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob26250a.txt
_cod_data_source_block           8ah_dk88
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_source_target' value 'MO' changed to 'Mo' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               7152764
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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
O1 O 0.12518(16) 0.75904(14) 1.13653(12) 0.0292(3) Uani 1 1 d
N1 N 0.22293(17) 0.80231(15) 0.93249(13) 0.0207(3) Uani 1 1 d
C1 C 0.1816(2) 0.85522(19) 1.05843(16) 0.0209(3) Uani 1 1 d
C2 C 0.21365(19) 1.02730(18) 1.09200(16) 0.0197(3) Uani 1 1 d
C3 C 0.27719(19) 1.13045(18) 0.99879(15) 0.0192(3) Uani 1 1 d
C4 C 0.30683(19) 1.06424(18) 0.86559(15) 0.0196(3) Uani 1 1 d
C5 C 0.2851(2) 0.90426(19) 0.83812(15) 0.0198(3) Uani 1 1 d
C6 C 0.3684(2) 1.17387(19) 0.76403(16) 0.0222(3) Uani 1 1 d
C7 C 0.2591(3) 1.2775(2) 0.71096(18) 0.0290(4) Uani 1 1 d
C8 C 0.2654(3) 1.1387(2) 0.61113(18) 0.0298(4) Uani 1 1 d
C9 C 0.1821(2) 1.0875(2) 1.22173(16) 0.0230(3) Uani 1 1 d
C10 C 0.2164(2) 1.2503(2) 1.25993(17) 0.0251(4) Uani 1 1 d
C11 C 0.2826(2) 1.3551(2) 1.16908(17) 0.0255(4) Uani 1 1 d
C12 C 0.3122(2) 1.29655(19) 1.04089(17) 0.0230(3) Uani 1 1 d
C13 C 0.3357(2) 0.8316(2) 0.71029(16) 0.0231(3) Uani 1 1 d
C14 C 0.1798(2) 0.7235(2) 0.58818(18) 0.0283(4) Uani 1 1 d
C15 C 0.2537(3) 0.6760(3) 0.4619(2) 0.0375(5) Uani 1 1 d
C16 C 0.1957(3) 0.6294(2) 0.90541(19) 0.0275(4) Uani 1 1 d
H6 H 0.500(3) 1.223(2) 0.7770(19) 0.025(4) Uiso 1 1 d
H7A H 0.150(3) 1.262(2) 0.744(2) 0.036(5) Uiso 1 1 d
H7B H 0.319(3) 1.384(3) 0.693(2) 0.035(5) Uiso 1 1 d
H8A H 0.336(3) 1.162(2) 0.535(2) 0.035(5) Uiso 1 1 d
H8B H 0.156(3) 1.047(2) 0.5859(19) 0.027(5) Uiso 1 1 d
H9 H 0.138(2) 1.009(2) 1.2837(19) 0.022(4) Uiso 1 1 d
H10 H 0.199(3) 1.294(2) 1.352(2) 0.036(5) Uiso 1 1 d
H11 H 0.306(3) 1.468(2) 1.197(2) 0.030(5) Uiso 1 1 d
H12 H 0.358(2) 1.372(2) 0.9781(19) 0.023(4) Uiso 1 1 d
H13A H 0.411(2) 0.925(2) 0.6742(18) 0.026(5) Uiso 1 1 d
H13B H 0.418(2) 0.771(2) 0.7434(18) 0.024(4) Uiso 1 1 d
H14A H 0.093(3) 0.783(2) 0.5607(19) 0.030(5) Uiso 1 1 d
H14B H 0.112(3) 0.629(2) 0.6177(19) 0.027(5) Uiso 1 1 d
H15A H 0.340(3) 0.619(3) 0.489(2) 0.052(6) Uiso 1 1 d
H15B H 0.318(3) 0.773(3) 0.426(2) 0.040(6) Uiso 1 1 d
H15C H 0.161(3) 0.609(3) 0.383(2) 0.043(6) Uiso 1 1 d
H16A H 0.233(3) 0.595(3) 0.990(2) 0.045(6) Uiso 1 1 d
H16B H 0.070(4) 0.566(3) 0.866(3) 0.060(7) Uiso 1 1 d
H16C H 0.267(4) 0.606(3) 0.841(3) 0.066(8) 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 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
C1 N1 C5 123.34(13)
C1 N1 C16 114.47(13)
C5 N1 C16 122.20(13)
O1 C1 N1 120.32(14)
O1 C1 C2 123.49(14)
N1 C1 C2 116.17(13)
C3 C2 C1 120.87(14)
C3 C2 C9 120.97(14)
C9 C2 C1 118.15(14)
C2 C3 C4 119.53(13)
C2 C3 C12 117.74(14)
C12 C3 C4 122.73(13)
C3 C4 C6 119.39(13)
C5 C4 C3 119.16(13)
C5 C4 C6 121.40(14)
N1 C5 C13 117.27(13)
C4 C5 N1 120.74(14)
C4 C5 C13 121.91(14)
C4 C6 C7 120.60(14)
C4 C6 C8 121.21(14)
C4 C6 H6 115.7(10)
C7 C6 H6 114.5(10)
C8 C6 C7 59.39(11)
C8 C6 H6 113.8(10)
C6 C7 H7A 114.2(12)
C6 C7 H7B 121.1(12)
C8 C7 C6 60.20(11)
C8 C7 H7A 116.4(12)
C8 C7 H7B 116.5(12)
H7A C7 H7B 116.6(17)
C6 C8 H8A 118.9(12)
C6 C8 H8B 115.8(11)
C7 C8 C6 60.42(11)
C7 C8 H8A 118.7(12)
C7 C8 H8B 115.4(11)
H8A C8 H8B 116.1(16)
C2 C9 H9 117.6(10)
C10 C9 C2 120.11(14)
C10 C9 H9 122.2(10)
C9 C10 C11 119.58(15)
C9 C10 H10 120.6(12)
C11 C10 H10 119.8(12)
C10 C11 H11 118.9(11)
C12 C11 C10 120.60(15)
C12 C11 H11 120.5(11)
C3 C12 H12 119.5(11)
C11 C12 C3 120.99(15)
C11 C12 H12 119.5(11)
C5 C13 C14 117.66(13)
C5 C13 H13A 105.5(10)
C5 C13 H13B 108.2(10)
C14 C13 H13A 109.0(10)
C14 C13 H13B 109.4(10)
H13A C13 H13B 106.5(14)
C13 C14 H14A 108.7(11)
C13 C14 H14B 110.7(11)
C15 C14 C13 110.79(14)
C15 C14 H14A 110.6(11)
C15 C14 H14B 109.1(11)
H14A C14 H14B 106.9(16)
C14 C15 H15A 110.9(13)
C14 C15 H15B 110.2(12)
C14 C15 H15C 113.7(13)
H15A C15 H15B 108.6(18)
H15A C15 H15C 107.9(19)
H15B C15 H15C 105.3(17)
N1 C16 H16A 110.3(13)
N1 C16 H16B 111.8(15)
N1 C16 H16C 111.0(16)
H16A C16 H16B 107.8(19)
H16A C16 H16C 107(2)
H16B C16 H16C 108(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2364(18)
N1 C1 1.392(2)
N1 C5 1.4024(19)
N1 C16 1.468(2)
C1 C2 1.457(2)
C2 C3 1.403(2)
C2 C9 1.409(2)
C3 C4 1.451(2)
C3 C12 1.411(2)
C4 C5 1.366(2)
C4 C6 1.498(2)
C5 C13 1.510(2)
C6 C7 1.517(2)
C6 C8 1.514(2)
C6 H6 0.973(19)
C7 C8 1.501(3)
C7 H7A 0.95(2)
C7 H7B 0.97(2)
C8 H8A 1.00(2)
C8 H8B 0.96(2)
C9 C10 1.379(2)
C9 H9 0.992(18)
C10 C11 1.400(2)
C10 H10 0.98(2)
C11 C12 1.384(2)
C11 H11 0.96(2)
C12 H12 0.984(19)
C13 C14 1.535(2)
C13 H13A 0.995(18)
C13 H13B 1.002(18)
C14 C15 1.522(3)
C14 H14A 1.005(19)
C14 H14B 0.950(19)
C15 H15A 0.99(2)
C15 H15B 0.99(2)
C15 H15C 0.96(2)
C16 H16A 0.94(2)
C16 H16B 0.96(3)
C16 H16C 0.96(3)
