#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/53/2225384.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_2225384
loop_
_publ_author_name
'Bohórquez, Arnold R. Romero'
'Kouznetsov, Vladimir V.'
'González, Teresa'
'Briceño, Alexander'
_publ_section_title
2-Ethyl-6-(2-pyridyl)-5,6,6a,11b-tetrahydro-7H-indeno[2,1-c]quinoline
_journal_coeditor_code           TK2615
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o680
_journal_page_last               o681
_journal_paper_doi               10.1107/S1600536810005805
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C23 H22 N2'
_chemical_formula_moiety         'C23 H22 N2'
_chemical_formula_sum            'C23 H22 N2'
_chemical_formula_weight         326.43
_chemical_name_common
;
2-Ethyl-6-(2-pyridinyl)-5,6,6a,11b-tetrahydro-7H
-indeno[2,1-c]quinoline
;
_chemical_name_systematic
;
2-Ethyl-6-(2-pyridyl)-5,6,6a,11b-tetrahydro-7H
-indeno[2,1-c]quinoline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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
_cell_angle_beta                 101.168(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.241(4)
_cell_length_b                   15.801(4)
_cell_length_c                   8.789(2)
_cell_measurement_reflns_used    11041
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      1.6
_cell_volume                     1804.0(8)
_computing_cell_refinement       'CrystalClear (Rigaku, 2002)'
_computing_data_collection       'CrystalClear (Rigaku, 2002)'
_computing_data_reduction        'CrystalClear (Rigaku, 2002)'
_computing_molecular_graphics
;
SHELXTL-NT (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998)
;
_computing_publication_material
;
SHELXTL-NT (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL-NT  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL-NT  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.85
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       'ω '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_av_sigmaI/netI    0.036
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20284
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         28.0
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.095
_refine_ls_R_factor_gt           0.058
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0698P)²+0.2578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.133
_refine_ls_wR_factor_ref         0.157
_reflns_number_gt                2420
_reflns_number_total             3688
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2615.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225384
_cod_database_fobs_code          2225384
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.02307(11) 0.64024(9) 0.43799(17) 0.0490(4) Uani d . 1 . .
H H1N -0.0192 0.6589 0.3565 0.059 Uiso d R 1 . .
N N2 -0.13358(12) 0.73555(10) 0.68890(19) 0.0562(4) Uani d . 1 . .
C C1 0.00785(13) 0.68474(11) 0.5771(2) 0.0460(4) Uani d . 1 . .
H H1 0.0242 0.7447 0.5668 0.055 Uiso calc R 1 . .
C C2 0.07995(13) 0.64878(11) 0.7193(2) 0.0458(4) Uani d . 1 . .
H H2 0.0741 0.6845 0.8084 0.055 Uiso calc R 1 . .
C C3 0.05427(14) 0.55713(11) 0.7591(2) 0.0528(5) Uani d . 1 . .
H H3A 0.0073 0.5563 0.8311 0.063 Uiso calc R 1 . .
H H3B 0.0237 0.5261 0.6663 0.063 Uiso calc R 1 . .
C C4 0.15662(15) 0.52035(11) 0.8317(2) 0.0499(5) Uani d . 1 . .
C C5 0.17744(17) 0.44613(13) 0.9155(2) 0.0636(6) Uani d . 1 . .
H H5 0.1240 0.4127 0.9366 0.076 Uiso calc R 1 . .
C C6 0.2788(2) 0.42241(15) 0.9675(3) 0.0744(7) Uani d . 1 . .
H H6 0.2934 0.3721 1.0223 0.089 Uiso calc R 1 . .
C C7 0.35794(19) 0.47219(16) 0.9391(3) 0.0766(7) Uani d . 1 . .
H H7 0.4257 0.4555 0.9753 0.092 Uiso calc R 1 . .
C C8 0.33764(16) 0.54720(14) 0.8568(2) 0.0653(6) Uani d . 1 . .
H H8 0.3915 0.5811 0.8387 0.078 Uiso calc R 1 . .
C C9 0.23611(14) 0.57118(11) 0.8019(2) 0.0485(5) Uani d . 1 . .
C C10 0.19475(13) 0.64765(11) 0.7040(2) 0.0456(4) Uani d . 1 . .
H H10 0.2292 0.6992 0.7495 0.055 Uiso calc R 1 . .
C C11 0.20897(13) 0.63816(10) 0.5372(2) 0.0434(4) Uani d . 1 . .
C C12 0.30732(15) 0.63126(11) 0.5033(2) 0.0523(5) Uani d . 1 . .
H H12 0.3636 0.6365 0.5845 0.063 Uiso calc R 1 . .
C C13 0.32582(15) 0.61707(12) 0.3557(2) 0.0540(5) Uani d . 1 . .
C C14 0.24015(16) 0.60999(12) 0.2362(2) 0.0545(5) Uani d . 1 . .
H H14 0.2494 0.5997 0.1356 0.065 Uiso calc R 1 . .
C C15 0.14227(14) 0.61795(11) 0.2647(2) 0.0485(5) Uani d . 1 . .
H H15 0.0864 0.6128 0.1828 0.058 Uiso calc R 1 . .
C C16 0.12446(13) 0.63354(10) 0.4138(2) 0.0427(4) Uani d . 1 . .
C C17 0.43476(17) 0.60998(15) 0.3268(3) 0.0731(7) Uani d . 1 . .
H H17A 0.4802 0.5943 0.4230 0.088 Uiso calc R 1 . .
H H17B 0.4371 0.5649 0.2526 0.088 Uiso calc R 1 . .
C C18 0.4737(2) 0.6887(2) 0.2677(5) 0.1291(13) Uani d . 1 . .
H H18A 0.5427 0.6798 0.2520 0.194 Uiso calc R 1 . .
H H18B 0.4734 0.7334 0.3416 0.194 Uiso calc R 1 . .
H H18C 0.4303 0.7040 0.1710 0.194 Uiso calc R 1 . .
C C19 -0.10323(13) 0.67742(11) 0.5962(2) 0.0459(4) Uani d . 1 . .
C C20 -0.16803(15) 0.61310(12) 0.5276(2) 0.0562(5) Uani d . 1 . .
H H20 -0.1446 0.5731 0.4650 0.067 Uiso calc R 1 . .
C C21 -0.26739(16) 0.60932(13) 0.5534(3) 0.0620(6) Uani d . 1 . .
H H21 -0.3120 0.5669 0.5082 0.074 Uiso calc R 1 . .
C C22 -0.29921(16) 0.66882(15) 0.6463(3) 0.0667(6) Uani d . 1 . .
H H22 -0.3660 0.6680 0.6650 0.080 Uiso calc R 1 . .
C C23 -0.23034(16) 0.73019(14) 0.7117(3) 0.0667(6) Uani d . 1 . .
H H23 -0.2525 0.7703 0.7755 0.080 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'
N N 0.0061 0.0033 '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
C16 N1 C1 . . 117.08(14) ?
C16 N1 H1N . . 112.5 ?
C1 N1 H1N . . 110.8 ?
C23 N2 C19 . . 117.16(17) ?
N1 C1 C19 . . 110.52(14) ?
N1 C1 C2 . . 109.93(14) ?
C19 C1 C2 . . 110.28(14) ?
N1 C1 H1 . . 108.7 ?
C19 C1 H1 . . 108.7 ?
C2 C1 H1 . . 108.7 ?
C1 C2 C3 . . 113.82(14) ?
C1 C2 C10 . . 113.60(14) ?
C3 C2 C10 . . 105.75(14) ?
C1 C2 H2 . . 107.8 ?
C3 C2 H2 . . 107.8 ?
C10 C2 H2 . . 107.8 ?
C4 C3 C2 . . 103.86(15) ?
C4 C3 H3A . . 111.0 ?
C2 C3 H3A . . 111.0 ?
C4 C3 H3B . . 111.0 ?
C2 C3 H3B . . 111.0 ?
H3A C3 H3B . . 109.0 ?
C5 C4 C9 . . 120.69(18) ?
C5 C4 C3 . . 128.74(18) ?
C9 C4 C3 . . 110.56(16) ?
C6 C5 C4 . . 119.1(2) ?
C6 C5 H5 . . 120.5 ?
C4 C5 H5 . . 120.5 ?
C7 C6 C5 . . 120.8(2) ?
C7 C6 H6 . . 119.6 ?
C5 C6 H6 . . 119.6 ?
C6 C7 C8 . . 120.5(2) ?
C6 C7 H7 . . 119.8 ?
C8 C7 H7 . . 119.8 ?
C7 C8 C9 . . 119.4(2) ?
C7 C8 H8 . . 120.3 ?
C9 C8 H8 . . 120.3 ?
C4 C9 C8 . . 119.61(19) ?
C4 C9 C10 . . 111.27(16) ?
C8 C9 C10 . . 129.09(18) ?
C11 C10 C9 . . 111.60(14) ?
C11 C10 C2 . . 113.02(14) ?
C9 C10 C2 . . 102.20(14) ?
C11 C10 H10 . . 109.9 ?
C9 C10 H10 . . 109.9 ?
C2 C10 H10 . . 109.9 ?
C12 C11 C16 . . 118.00(17) ?
C12 C11 C10 . . 120.53(16) ?
C16 C11 C10 . . 121.44(16) ?
C13 C12 C11 . . 123.67(18) ?
C13 C12 H12 . . 118.2 ?
C11 C12 H12 . . 118.2 ?
C12 C13 C14 . . 116.96(18) ?
C12 C13 C17 . . 121.04(18) ?
C14 C13 C17 . . 122.00(18) ?
C15 C14 C13 . . 120.98(18) ?
C15 C14 H14 . . 119.5 ?
C13 C14 H14 . . 119.5 ?
C14 C15 C16 . . 121.60(17) ?
C14 C15 H15 . . 119.2 ?
C16 C15 H15 . . 119.2 ?
C15 C16 C11 . . 118.71(17) ?
C15 C16 N1 . . 119.70(16) ?
C11 C16 N1 . . 121.53(16) ?
C18 C17 C13 . . 113.9(2) ?
C18 C17 H17A . . 108.8 ?
C13 C17 H17A . . 108.8 ?
C18 C17 H17B . . 108.8 ?
C13 C17 H17B . . 108.8 ?
H17A C17 H17B . . 107.7 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
N2 C19 C20 . . 122.16(17) ?
N2 C19 C1 . . 115.24(15) ?
C20 C19 C1 . . 122.56(16) ?
C21 C20 C19 . . 119.26(18) ?
C21 C20 H20 . . 120.4 ?
C19 C20 H20 . . 120.4 ?
C22 C21 C20 . . 118.92(19) ?
C22 C21 H21 . . 120.5 ?
C20 C21 H21 . . 120.5 ?
C21 C22 C23 . . 118.6(2) ?
C21 C22 H22 . . 120.7 ?
C23 C22 H22 . . 120.7 ?
N2 C23 C22 . . 123.90(19) ?
N2 C23 H23 . . 118.1 ?
C22 C23 H23 . . 118.1 ?
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
N1 C16 . 1.403(2) ?
N1 C1 . 1.458(2) ?
N1 H1N . 0.8700 ?
N2 C23 . 1.337(2) ?
N2 C19 . 1.340(2) ?
C1 C19 . 1.517(2) ?
C1 C2 . 1.528(2) ?
C1 H1 . 0.9800 ?
C2 C3 . 1.543(2) ?
C2 C10 . 1.552(2) ?
C2 H2 . 0.9800 ?
C3 C4 . 1.499(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.384(3) ?
C4 C9 . 1.389(3) ?
C5 C6 . 1.383(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.371(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.387(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.390(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.522(2) ?
C10 C11 . 1.521(2) ?
C10 H10 . 0.9800 ?
C11 C12 . 1.395(3) ?
C11 C16 . 1.401(2) ?
C12 C13 . 1.384(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.393(3) ?
C13 C17 . 1.516(3) ?
C14 C15 . 1.373(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.397(2) ?
C15 H15 . 0.9300 ?
C17 C18 . 1.479(3) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 C20 . 1.390(3) ?
C20 C21 . 1.379(3) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.364(3) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.378(3) ?
C22 H22 . 0.9300 ?
C23 H23 . 0.9300 ?
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
N1 H1N N2 4_575 0.87 2.53 3.345(2) 157 yes
C20 H20 N1 1_555 0.93 2.51 2.825(3) 100 yes
C14 H14 Cg4 1_554 0.93 2.74 3.611(2) 153 yes
