#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/34/2213434.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2213434
loop_
_publ_author_name
'Kandinska, Meglena I.'
'Todorov, Iliya S.'
'Boris Shivachev'
'Bogdanov, Milen G.'
_publ_section_title
;trans-rac-2-Hexyl-1-oxo-3-(2-pyridyl)-1,2,3,4-tetrahydroisoquinoline-4-carboxylic
 acid
;
_journal_coeditor_code           LH2313
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2544
_journal_page_last               o2546
_journal_paper_doi               10.1107/S1600536807010562
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C21 H24 N2 O3'
_chemical_formula_moiety         'C21 H24 N2 O3'
_chemical_formula_sum            'C21 H24 N2 O3'
_chemical_formula_weight         352.42
_chemical_melting_point          389
_chemical_name_systematic
'trans-rac-2-Hexyl-1-oxo-3-(2-pyridyl)-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid'
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.216(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8917(4)
_cell_length_b                   12.9205(9)
_cell_length_c                   15.5882(9)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      11.636
_cell_measurement_theta_min      8.167
_cell_volume                     1939.5(2)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and MERCURY (Version 1.4; Macrae
et al.,  2006)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'Non-profiled ω/2θ'
_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  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3907
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        -1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.0894
_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)+(0.1806P)²+0.5652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2519
_refine_ls_wR_factor_ref         0.2918
_reflns_number_gt                2371
_reflns_number_total             3770
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2313.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2213434
_cod_database_fobs_code          2213434
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.5371(2) 0.32470(19) 0.75690(19) 0.0754(8) Uani d . 1
H H1 0.5690 0.2580 0.7450 0.113 Uiso d R 1
O O2 0.9082(2) 0.63213(18) 0.77527(18) 0.0671(7) Uani d . 1
O O3 0.7486(3) 0.3350(2) 0.8398(2) 0.0922(11) Uani d . 1
N N1 0.6857(3) 0.5773(2) 0.73663(18) 0.0525(7) Uani d . 1
N N2 0.3546(3) 0.6176(3) 0.8012(2) 0.0724(9) Uani d . 1
C C1 0.8024(3) 0.6005(2) 0.7976(2) 0.0518(8) Uani d . 1
C C2 0.8010(3) 0.5845(2) 0.8909(2) 0.0507(8) Uani d . 1
C C3 0.9065(4) 0.6258(3) 0.9571(3) 0.0648(10) Uani d . 1
H H3 0.9749 0.6668 0.9421 0.078 Uiso calc R 1
C C4 0.9102(4) 0.6065(3) 1.0438(3) 0.0767(12) Uani d . 1
H H4 0.9805 0.6348 1.0875 0.092 Uiso calc R 1
C C5 0.8093(4) 0.5446(3) 1.0666(3) 0.0755(11) Uani d . 1
H H5 0.8125 0.5313 1.1256 0.091 Uiso calc R 1
C C6 0.7053(4) 0.5031(3) 1.0027(2) 0.0639(9) Uani d . 1
H H6 0.6382 0.4615 1.0185 0.077 Uiso calc R 1
C C7 0.6993(3) 0.5228(2) 0.9143(2) 0.0507(8) Uani d . 1
C C8 0.5907(3) 0.4758(2) 0.8417(2) 0.0510(8) Uani d . 1
H H8 0.5059 0.4662 0.8633 0.061 Uiso calc R 1
C C9 0.5578(3) 0.5491(2) 0.7628(2) 0.0513(8) Uani d . 1
H H9 0.5001 0.5106 0.7136 0.062 Uiso calc R 1
C C10 0.4735(3) 0.6428(3) 0.7799(2) 0.0537(8) Uani d . 1
C C11 0.2733(4) 0.6959(4) 0.8148(3) 0.0884(14) Uani d . 1
H H11 0.1908 0.6800 0.8309 0.106 Uiso calc R 1
C C12 0.3050(4) 0.7987(4) 0.8062(3) 0.0827(13) Uani d . 1
H H12 0.2448 0.8505 0.8156 0.099 Uiso calc R 1
C C13 0.4258(4) 0.8227(3) 0.7837(3) 0.0710(10) Uani d . 1
H H13 0.4501 0.8915 0.7782 0.085 Uiso calc R 1
C C14 0.5132(3) 0.7436(3) 0.7688(2) 0.0614(9) Uani d . 1
H H14 0.5955 0.7580 0.7519 0.074 Uiso calc R 1
C C15 0.6356(3) 0.3708(2) 0.8141(2) 0.0541(8) Uani d . 1
C C16 0.6813(4) 0.5874(3) 0.6430(2) 0.0612(9) Uani d . 1
H H16A 0.7462 0.6408 0.6350 0.073 Uiso calc R 1
H H16B 0.5890 0.6096 0.6127 0.073 Uiso calc R 1
C C17 0.7161(4) 0.4887(3) 0.6013(3) 0.0732(11) Uani d . 1
H H17A 0.6496 0.4357 0.6077 0.088 Uiso calc R 1
H H17B 0.8074 0.4654 0.6325 0.088 Uiso calc R 1
C C18 0.7151(5) 0.5006(4) 0.5049(3) 0.0907(14) Uani d . 1
H H18A 0.7821 0.5535 0.4992 0.109 Uiso calc R 1
H H18B 0.6242 0.5254 0.4746 0.109 Uiso calc R 1
C C19 0.7477(7) 0.4033(6) 0.4583(4) 0.125(2) Uani d . 1
H H19A 0.6821 0.3500 0.4655 0.150 Uiso calc R 1
H H19B 0.7318 0.4182 0.3959 0.150 Uiso calc R 1
C C20 0.8796(8) 0.3637(6) 0.4859(6) 0.152(3) Uani d . 1
H H20A 0.8880 0.3390 0.5456 0.182 Uiso calc R 1
H H20B 0.9433 0.4214 0.4894 0.182 Uiso calc R 1
C C21 0.9324(7) 0.2802(5) 0.4374(5) 0.145(3) Uani d . 1
H H21A 1.0229 0.2593 0.4697 0.217 Uiso calc R 1
H H21B 0.9383 0.3050 0.3803 0.217 Uiso calc R 1
H H21C 0.8704 0.2221 0.4307 0.217 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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_publ_flag
C15 O1 H1 108.6 ?
C1 N1 C16 120.7(3) ?
C1 N1 C9 120.9(3) y
C16 N1 C9 118.2(3) y
C10 N2 C11 116.8(3) ?
O2 C1 N1 120.9(3) ?
O2 C1 C2 121.4(3) ?
N1 C1 C2 117.7(3) ?
C3 C2 C7 119.1(3) ?
C3 C2 C1 120.2(3) ?
C7 C2 C1 120.6(3) ?
C4 C3 C2 120.5(4) ?
C4 C3 H3 119.7 ?
C2 C3 H3 119.7 ?
C3 C4 C5 120.0(4) ?
C3 C4 H4 120.0 ?
C5 C4 H4 120.0 ?
C6 C5 C4 120.4(4) ?
C6 C5 H5 119.8 ?
C4 C5 H5 119.8 ?
C5 C6 C7 120.3(4) ?
C5 C6 H6 119.8 ?
C7 C6 H6 119.8 ?
C6 C7 C2 119.6(3) ?
C6 C7 C8 122.4(3) ?
C2 C7 C8 117.9(3) ?
C7 C8 C15 111.7(2) y
C7 C8 C9 109.9(3) ?
C15 C8 C9 110.3(3) ?
C7 C8 H8 108.3 ?
C15 C8 H8 108.3 ?
C9 C8 H8 108.3 ?
N1 C9 C8 110.0(2) y
N1 C9 C10 113.1(3) y
C8 C9 C10 112.0(3) y
N1 C9 H9 107.1 ?
C8 C9 H9 107.1 ?
C10 C9 H9 107.1 ?
N2 C10 C14 123.6(3) ?
N2 C10 C9 113.4(3) ?
C14 C10 C9 122.9(3) ?
N2 C11 C12 123.7(4) ?
N2 C11 H11 118.2 ?
C12 C11 H11 118.2 ?
C13 C12 C11 118.6(4) ?
C13 C12 H12 120.7 ?
C11 C12 H12 120.7 ?
C12 C13 C14 119.5(4) ?
C12 C13 H13 120.2 ?
C14 C13 H13 120.2 ?
C10 C14 C13 117.8(3) ?
C10 C14 H14 121.1 ?
C13 C14 H14 121.1 ?
O3 C15 O1 123.3(3) ?
O3 C15 C8 124.4(3) ?
O1 C15 C8 112.3(3) ?
N1 C16 C17 113.5(3) ?
N1 C16 H16A 108.9 ?
C17 C16 H16A 108.9 ?
N1 C16 H16B 108.9 ?
C17 C16 H16B 108.9 ?
H16A C16 H16B 107.7 ?
C16 C17 C18 113.1(3) ?
C16 C17 H17A 109.0 ?
C18 C17 H17A 109.0 ?
C16 C17 H17B 109.0 ?
C18 C17 H17B 109.0 ?
H17A C17 H17B 107.8 ?
C17 C18 C19 115.9(5) ?
C17 C18 H18A 108.3 ?
C19 C18 H18A 108.3 ?
C17 C18 H18B 108.3 ?
C19 C18 H18B 108.3 ?
H18A C18 H18B 107.4 ?
C20 C19 C18 116.6(6) ?
C20 C19 H19A 108.1 ?
C18 C19 H19A 108.1 ?
C20 C19 H19B 108.1 ?
C18 C19 H19B 108.1 ?
H19A C19 H19B 107.3 ?
C19 C20 C21 122.2(7) ?
C19 C20 H20A 106.8 ?
C21 C20 H20A 106.8 ?
C19 C20 H20B 106.8 ?
C21 C20 H20B 106.8 ?
H20A C20 H20B 106.6 ?
C20 C21 H21A 109.5 ?
C20 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C20 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C15 1.305(4) y
O1 H1 0.9502 ?
O2 C1 1.245(4) y
O3 C15 1.191(4) y
N1 C1 1.351(4) y
N1 C16 1.456(4) ?
N1 C9 1.461(4) ?
N2 C10 1.334(4) ?
N2 C11 1.339(5) ?
C1 C2 1.472(5) ?
C2 C3 1.395(5) ?
C2 C7 1.396(4) ?
C3 C4 1.366(6) ?
C3 H3 0.9300 ?
C4 C5 1.387(6) ?
C4 H4 0.9300 ?
C5 C6 1.367(5) ?
C5 H5 0.9300 ?
C6 C7 1.389(5) ?
C6 H6 0.9300 ?
C7 C8 1.500(5) ?
C8 C15 1.519(4) ?
C8 C9 1.527(5) ?
C8 H8 0.9800 ?
C9 C10 1.529(4) ?
C9 H9 0.9800 ?
C10 C14 1.382(5) ?
C11 C12 1.379(6) ?
C11 H11 0.9300 ?
C12 C13 1.356(6) ?
C12 H12 0.9300 ?
C13 C14 1.392(5) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C16 C17 1.507(5) ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
C17 C18 1.507(6) ?
C17 H17A 0.9700 ?
C17 H17B 0.9700 ?
C18 C19 1.523(7) ?
C18 H18A 0.9700 ?
C18 H18B 0.9700 ?
C19 C20 1.376(8) ?
C19 H19A 0.9700 ?
C19 H19B 0.9700 ?
C20 C21 1.479(8) ?
C20 H20A 0.9700 ?
C20 H20B 0.9700 ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O2 2_646 0.95 1.68 2.619(2) 168.0 yes
C4 H4 O3 3_767 0.93 2.69 3.529(3) 150.6 yes
C14 H14 O3 2_656 0.93 2.53 3.411(3) 157.4 yes
C16 H16A O3 2_656 0.97 2.54 3.271(3) 132.4 yes
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
_geom_torsion_publ_flag
C9 N1 C1 O2 -174.5(3) y
C9 N1 C1 C2 7.1(4) ?
C16 N1 C1 O2 0.7(4) ?
C16 N1 C1 C2 -177.6(3) ?
C1 N1 C9 C8 -42.5(4) y
C1 N1 C9 C10 83.5(3) ?
C16 N1 C9 C8 142.1(3) y
C16 N1 C9 C10 -91.8(3) y
C1 N1 C16 C17 93.3(4) ?
C9 N1 C16 C17 -91.3(4) ?
C11 N2 C10 C9 -178.2(3) ?
C11 N2 C10 C14 -2.2(6) ?
C10 N2 C11 C12 1.3(7) ?
O2 C1 C2 C3 14.4(4) ?
O2 C1 C2 C7 -161.6(3) ?
N1 C1 C2 C3 -167.2(3) ?
N1 C1 C2 C7 16.7(4) ?
C1 C2 C3 C4 -176.4(3) ?
C7 C2 C3 C4 -0.2(5) ?
C1 C2 C7 C6 175.8(3) ?
C1 C2 C7 C8 -1.3(4) y
C3 C2 C7 C6 -0.4(4) ?
C3 C2 C7 C8 -177.4(3) ?
C2 C3 C4 C5 0.6(6) ?
C3 C4 C5 C6 -0.4(6) ?
C4 C5 C6 C7 -0.2(6) ?
C5 C6 C7 C2 0.6(5) ?
C5 C6 C7 C8 177.5(3) ?
C2 C7 C8 C9 -33.7(4) ?
C2 C7 C8 C15 89.1(3) ?
C6 C7 C8 C9 149.3(3) ?
C6 C7 C8 C15 -87.9(4) ?
C7 C8 C9 N1 53.7(3) ?
C7 C8 C9 C10 -73.0(3) ?
C15 C8 C9 N1 -69.9(3) ?
C15 C8 C9 C10 163.4(2) y
C7 C8 C15 O1 174.0(3) ?
C7 C8 C15 O3 -7.6(5) ?
C9 C8 C15 O1 -63.5(4) ?
C9 C8 C15 O3 114.9(4) ?
N1 C9 C10 N2 178.1(3) ?
N1 C9 C10 C14 2.0(5) ?
C8 C9 C10 N2 -57.0(4) ?
C8 C9 C10 C14 126.9(3) ?
N2 C10 C14 C13 2.3(6) ?
C9 C10 C14 C13 178.0(3) ?
N2 C11 C12 C13 -0.7(8) ?
C11 C12 C13 C14 0.8(7) ?
C12 C13 C14 C10 -1.6(6) ?
N1 C16 C17 C18 -178.4(3) ?
C16 C17 C18 C19 -179.3(4) ?
C17 C18 C19 C20 -65.4(8) ?
C18 C19 C20 C21 -169.9(7) ?
H1 O1 C15 O3 5.2 ?
H1 O1 C15 C8 -176.4 ?
C1 N1 C9 H9 -158.6 ?
C16 N1 C9 H9 26.0 ?
C1 N1 C16 H16A -28.1 ?
C1 N1 C16 H16B -145.3 ?
C9 N1 C16 H16A 147.3 ?
C9 N1 C16 H16B 30.1 ?
C10 N2 C11 H11 -178.7 ?
C1 C2 C3 H3 3.6 ?
C7 C2 C3 H3 179.8 ?
C2 C3 C4 H4 -179.4 ?
H3 C3 C4 C5 -179.4 ?
H3 C3 C4 H4 0.6 ?
C3 C4 C5 H5 179.6 ?
H4 C4 C5 C6 179.6 ?
H4 C4 C5 H5 -0.4 ?
C4 C5 C6 H6 179.8 ?
H5 C5 C6 C7 179.8 ?
H5 C5 C6 H6 -0.2 ?
H6 C6 C7 C2 -179.4 ?
H6 C6 C7 C8 -2.5 ?
C2 C7 C8 H8 -151.8 ?
C6 C7 C8 H8 31.3 ?
C7 C8 C9 H9 169.8 ?
C15 C8 C9 H9 46.2 ?
H8 C8 C9 N1 171.8 ?
H8 C8 C9 C10 45.1 ?
H8 C8 C9 H9 -72.1 ?
H8 C8 C15 O1 54.8 ?
H8 C8 C15 O3 -126.7 ?
H9 C9 C10 N2 60.2 ?
H9 C9 C10 C14 -115.9 ?
N2 C10 C14 H14 -177.7 ?
C9 C10 C14 H14 -2.0 ?
N2 C11 C12 H12 179.3 ?
H11 C11 C12 C13 179.3 ?
H11 C11 C12 H12 -0.7 ?
C11 C12 C13 H13 -179.2 ?
H12 C12 C13 C14 -179.2 ?
H12 C12 C13 H13 0.8 ?
C12 C13 C14 H14 178.4 ?
H13 C13 C14 C10 178.4 ?
H13 C13 C14 H14 -1.6 ?
N1 C16 C17 H17A 60.2 ?
N1 C16 C17 H17B -57.1 ?
H16A C16 C17 C18 -57.0 ?
H16A C16 C17 H17A -178.4 ?
H16A C16 C17 H17B 64.3 ?
H16B C16 C17 C18 60.1 ?
H16B C16 C17 H17A -61.2 ?
H16B C16 C17 H17B -178.5 ?
C16 C17 C18 H18A 58.8 ?
C16 C17 C18 H18B -57.4 ?
H17A C17 C18 C19 -57.9 ?
H17A C17 C18 H18A -179.8 ?
H17A C17 C18 H18B 64.0 ?
H17B C17 C18 C19 59.4 ?
H17B C17 C18 H18A -62.5 ?
H17B C17 C18 H18B -178.7 ?
C17 C18 C19 H19A 56.6 ?
C17 C18 C19 H19B 172.5 ?
H18A C18 C19 C20 56.4 ?
H18A C18 C19 H19A 178.5 ?
H18A C18 C19 H19B -65.6 ?
H18B C18 C19 C20 172.7 ?
H18B C18 C19 H19A -65.3 ?
H18B C18 C19 H19B 50.6 ?
C18 C19 C20 H20A 66.9 ?
