#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/44/2224401.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_2224401
loop_
_publ_author_name
'Porosa, Lukasz'
'Viirre, Russell D.'
'Lough, Alan J.'
_publ_section_title
N,1-Bis(4-chloro-2-methylbenzyl)-3-methyl-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxamide
_journal_coeditor_code           PV2230
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3090
_journal_paper_doi               10.1107/S1600536809046765
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C27 H26 Cl2 N2 O2'
_chemical_formula_moiety         'C27 H26 Cl2 N2 O2'
_chemical_formula_sum            'C27 H26 Cl2 N2 O2'
_chemical_formula_weight         481.40
_chemical_name_systematic
;
N,1-Bis(4-chloro-2-methylbenzyl)-3-methyl-2-oxo-1,2,3,4-
tetrahydroquinoline-3-carboxamide
;
_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
_cell_angle_alpha                82.084(3)
_cell_angle_beta                 71.403(3)
_cell_angle_gamma                66.519(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1394(6)
_cell_length_b                   10.7095(6)
_cell_length_c                   12.2542(4)
_cell_measurement_reflns_used    10842
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1156.66(10)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0667
_diffrn_reflns_av_sigmaI/netI    0.0883
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10842
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.57
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
from symmetry-related measurements (SORTAV; Blessing, 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0640
_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)+(0.0886P)²+0.0727P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1840
_reflns_number_gt                2859
_reflns_number_total             5170
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2230.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2224401
_cod_database_fobs_code          2224401
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.21891(11) 0.99149(9) 1.07942(7) 0.0631(3) Uani d . 1 . .
Cl Cl2 0.43748(10) 0.28380(10) -0.14948(6) 0.0707(3) Uani d . 1 . .
O O1 0.4463(2) 0.5129(2) 0.39762(16) 0.0514(6) Uani d . 1 . .
O O2 0.0270(2) 0.8179(2) 0.61445(16) 0.0507(6) Uani d . 1 . .
N N1 0.2188(3) 0.5470(2) 0.37995(18) 0.0405(6) Uani d . 1 . .
N N2 0.2249(3) 0.6438(2) 0.65164(18) 0.0424(6) Uani d . 1 . .
H H1N 0.3172 0.5853 0.6235 0.051 Uiso calc R 1 . .
C C1 0.3161(4) 0.5882(3) 0.4071(2) 0.0408(7) Uani d . 1 . .
C C2 0.2518(3) 0.7334(3) 0.4536(2) 0.0405(7) Uani d . 1 . .
C C3 0.1526(3) 0.8275(3) 0.3812(2) 0.0430(7) Uani d . 1 . .
H H3A 0.1013 0.9195 0.4152 0.052 Uiso calc R 1 . .
H H3B 0.2167 0.8351 0.3025 0.052 Uiso calc R 1 . .
C C4 0.0378(3) 0.7782(3) 0.3742(2) 0.0411(7) Uani d . 1 . .
C C5 -0.1028(4) 0.8655(3) 0.3656(2) 0.0497(8) Uani d . 1 . .
H H5A -0.1286 0.9611 0.3659 0.060 Uiso calc R 1 . .
C C6 -0.2068(4) 0.8164(4) 0.3567(2) 0.0548(9) Uani d . 1 . .
H H6A -0.3029 0.8779 0.3516 0.066 Uiso calc R 1 . .
C C7 -0.1698(4) 0.6789(4) 0.3551(2) 0.0474(8) Uani d . 1 . .
H H7A -0.2405 0.6453 0.3482 0.057 Uiso calc R 1 . .
C C8 -0.0307(4) 0.5881(3) 0.3635(2) 0.0453(8) Uani d . 1 . .
H H8A -0.0058 0.4928 0.3619 0.054 Uiso calc R 1 . .
C C9 0.0724(3) 0.6375(3) 0.3742(2) 0.0392(7) Uani d . 1 . .
C C10 0.3780(3) 0.7793(3) 0.4494(2) 0.0474(8) Uani d . 1 . .
H H10A 0.3347 0.8697 0.4836 0.071 Uiso calc R 1 . .
H H10B 0.4370 0.7834 0.3692 0.071 Uiso calc R 1 . .
H H10C 0.4433 0.7143 0.4928 0.071 Uiso calc R 1 . .
C C11 0.1555(3) 0.7353(3) 0.5808(2) 0.0411(7) Uani d . 1 . .
C C12 0.1485(4) 0.6406(3) 0.7743(2) 0.0430(7) Uani d . 1 . .
H H12A 0.1870 0.5458 0.8029 0.052 Uiso calc R 1 . .
H H12B 0.0400 0.6670 0.7844 0.052 Uiso calc R 1 . .
C C13 0.1659(3) 0.7323(3) 0.8486(2) 0.0391(7) Uani d . 1 . .
C C14 0.2568(3) 0.8058(3) 0.8039(2) 0.0436(8) Uani d . 1 . .
H H14A 0.3098 0.7996 0.7242 0.052 Uiso calc R 1 . .
C C15 0.2724(4) 0.8887(3) 0.8728(3) 0.0475(8) Uani d . 1 . .
H H15A 0.3325 0.9413 0.8407 0.057 Uiso calc R 1 . .
C C16 0.1988(4) 0.8925(3) 0.9887(3) 0.0448(8) Uani d . 1 . .
C C17 0.1071(4) 0.8214(3) 1.0353(2) 0.0443(8) Uani d . 1 . .
H H17A 0.0565 0.8265 1.1155 0.053 Uiso calc R 1 . .
C C18 0.0882(3) 0.7424(3) 0.9662(2) 0.0409(7) Uani d . 1 . .
C C19 -0.0146(4) 0.6665(4) 1.0202(3) 0.0611(10) Uani d . 1 . .
H H19A -0.0770 0.7029 1.0969 0.092 Uiso calc R 1 . .
H H19B 0.0457 0.5696 1.0270 0.092 Uiso calc R 1 . .
H H19C -0.0793 0.6777 0.9719 0.092 Uiso calc R 1 . .
C C20 0.2704(4) 0.4028(3) 0.3528(2) 0.0426(7) Uani d . 1 . .
H H20A 0.1903 0.3687 0.3957 0.051 Uiso calc R 1 . .
H H20B 0.3596 0.3506 0.3801 0.051 Uiso calc R 1 . .
C C21 0.3107(3) 0.3756(3) 0.2262(2) 0.0353(7) Uani d . 1 . .
C C22 0.3173(3) 0.4763(3) 0.1428(2) 0.0443(8) Uani d . 1 . .
H H22A 0.2943 0.5657 0.1655 0.053 Uiso calc R 1 . .
C C23 0.3568(3) 0.4491(3) 0.0266(2) 0.0454(8) Uani d . 1 . .
H H23A 0.3613 0.5185 -0.0301 0.055 Uiso calc R 1 . .
C C24 0.3888(3) 0.3208(3) -0.0038(2) 0.0441(8) Uani d . 1 . .
C C25 0.3860(3) 0.2177(3) 0.0767(2) 0.0454(8) Uani d . 1 . .
H H25A 0.4117 0.1284 0.0523 0.054 Uiso calc R 1 . .
C C26 0.3458(3) 0.2435(3) 0.1934(2) 0.0387(7) Uani d . 1 . .
C C27 0.3438(4) 0.1298(3) 0.2814(3) 0.0522(8) Uani d . 1 . .
H H27A 0.3800 0.0437 0.2417 0.078 Uiso calc R 1 . .
H H27B 0.2409 0.1496 0.3314 0.078 Uiso calc R 1 . .
H H27C 0.4092 0.1224 0.3280 0.078 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C9 . . 123.4(2) ?
C1 N1 C20 . . 117.6(2) ?
C9 N1 C20 . . 119.0(2) ?
C11 N2 C12 . . 120.7(2) ?
C11 N2 H1N . . 119.7 ?
C12 N2 H1N . . 119.7 ?
O1 C1 N1 . . 121.9(3) ?
O1 C1 C2 . . 121.4(3) ?
N1 C1 C2 . . 116.6(3) ?
C3 C2 C10 . . 111.2(2) ?
C3 C2 C1 . . 108.0(2) ?
C10 C2 C1 . . 110.8(2) ?
C3 C2 C11 . . 109.5(2) ?
C10 C2 C11 . . 108.2(2) ?
C1 C2 C11 . . 109.1(2) ?
C4 C3 C2 . . 112.5(2) ?
C4 C3 H3A . . 109.1 ?
C2 C3 H3A . . 109.1 ?
C4 C3 H3B . . 109.1 ?
C2 C3 H3B . . 109.1 ?
H3A C3 H3B . . 107.8 ?
C5 C4 C9 . . 118.0(3) ?
C5 C4 C3 . . 122.7(3) ?
C9 C4 C3 . . 119.3(3) ?
C4 C5 C6 . . 121.5(3) ?
C4 C5 H5A . . 119.3 ?
C6 C5 H5A . . 119.3 ?
C7 C6 C5 . . 119.5(3) ?
C7 C6 H6A . . 120.2 ?
C5 C6 H6A . . 120.2 ?
C6 C7 C8 . . 120.9(3) ?
C6 C7 H7A . . 119.6 ?
C8 C7 H7A . . 119.6 ?
C7 C8 C9 . . 119.4(3) ?
C7 C8 H8A . . 120.3 ?
C9 C8 H8A . . 120.3 ?
C8 C9 C4 . . 120.7(3) ?
C8 C9 N1 . . 121.1(3) ?
C4 C9 N1 . . 118.2(3) ?
C2 C10 H10A . . 109.5 ?
C2 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C2 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O2 C11 N2 . . 122.7(3) ?
O2 C11 C2 . . 121.6(3) ?
N2 C11 C2 . . 115.6(2) ?
N2 C12 C13 . . 115.5(2) ?
N2 C12 H12A . . 108.4 ?
C13 C12 H12A . . 108.4 ?
N2 C12 H12B . . 108.4 ?
C13 C12 H12B . . 108.4 ?
H12A C12 H12B . . 107.5 ?
C14 C13 C18 . . 118.7(3) ?
C14 C13 C12 . . 122.1(2) ?
C18 C13 C12 . . 119.2(3) ?
C13 C14 C15 . . 121.5(3) ?
C13 C14 H14A . . 119.2 ?
C15 C14 H14A . . 119.2 ?
C16 C15 C14 . . 118.3(3) ?
C16 C15 H15A . . 120.9 ?
C14 C15 H15A . . 120.9 ?
C17 C16 C15 . . 121.5(3) ?
C17 C16 Cl1 . . 118.5(2) ?
C15 C16 Cl1 . . 120.0(3) ?
C16 C17 C18 . . 120.1(3) ?
C16 C17 H17A . . 119.9 ?
C18 C17 H17A . . 119.9 ?
C17 C18 C13 . . 119.8(3) ?
C17 C18 C19 . . 118.7(3) ?
C13 C18 C19 . . 121.5(3) ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
N1 C20 C21 . . 114.2(2) ?
N1 C20 H20A . . 108.7 ?
C21 C20 H20A . . 108.7 ?
N1 C20 H20B . . 108.7 ?
C21 C20 H20B . . 108.7 ?
H20A C20 H20B . . 107.6 ?
C22 C21 C26 . . 119.7(2) ?
C22 C21 C20 . . 122.0(3) ?
C26 C21 C20 . . 118.3(2) ?
C21 C22 C23 . . 121.3(3) ?
C21 C22 H22A . . 119.4 ?
C23 C22 H22A . . 119.4 ?
C24 C23 C22 . . 118.3(3) ?
C24 C23 H23A . . 120.8 ?
C22 C23 H23A . . 120.8 ?
C23 C24 C25 . . 121.9(3) ?
C23 C24 Cl2 . . 119.3(2) ?
C25 C24 Cl2 . . 118.8(2) ?
C24 C25 C26 . . 120.5(3) ?
C24 C25 H25A . . 119.8 ?
C26 C25 H25A . . 119.8 ?
C25 C26 C21 . . 118.3(3) ?
C25 C26 C27 . . 120.3(3) ?
C21 C26 C27 . . 121.4(2) ?
C26 C27 H27A . . 109.5 ?
C26 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C26 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C16 . 1.744(3) ?
Cl2 C24 . 1.750(3) ?
O1 C1 . 1.219(3) ?
O2 C11 . 1.220(3) ?
N1 C1 . 1.369(4) ?
N1 C9 . 1.432(4) ?
N1 C20 . 1.468(4) ?
N2 C11 . 1.347(4) ?
N2 C12 . 1.458(3) ?
N2 H1N . 0.8800 ?
C1 C2 . 1.539(4) ?
C2 C3 . 1.526(4) ?
C2 C10 . 1.528(4) ?
C2 C11 . 1.551(4) ?
C3 C4 . 1.486(4) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.387(4) ?
C4 C9 . 1.404(4) ?
C5 C6 . 1.390(5) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.369(5) ?
C6 H6A . 0.9500 ?
C7 C8 . 1.385(4) ?
C7 H7A . 0.9500 ?
C8 C9 . 1.392(4) ?
C8 H8A . 0.9500 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C12 C13 . 1.519(4) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.381(4) ?
C13 C18 . 1.400(4) ?
C14 C15 . 1.389(4) ?
C14 H14A . 0.9500 ?
C15 C16 . 1.375(4) ?
C15 H15A . 0.9500 ?
C16 C17 . 1.370(4) ?
C17 C18 . 1.379(4) ?
C17 H17A . 0.9500 ?
C18 C19 . 1.507(4) ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C20 C21 . 1.511(3) ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C21 C22 . 1.387(4) ?
C21 C26 . 1.398(4) ?
C22 C23 . 1.389(4) ?
C22 H22A . 0.9500 ?
C23 C24 . 1.357(4) ?
C23 H23A . 0.9500 ?
C24 C25 . 1.379(4) ?
C25 C26 . 1.390(4) ?
C25 H25A . 0.9500 ?
C26 C27 . 1.513(4) ?
C27 H27A . 0.9800 ?
C27 H27B . 0.9800 ?
C27 H27C . 0.9800 ?
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
N2 H1N O1 2_666 0.88 2.14 2.972(3) 156.9
