#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/55/2015576.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_2015576
loop_
_publ_author_name
'Abhijit Mitra'
'Pamela J. Seaton'
'Kraig A. Wheeler'
_publ_section_title
;
 N-(2-Aminobenzyl)-N,N-bis(quinolin-2-ylmethyl)amine
;
_journal_coeditor_code           SF3012
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o581
_journal_page_last               o582
_journal_paper_doi               10.1107/S0108270106030502
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C27 H24 N4'
_chemical_formula_moiety         'C27 H24 N4'
_chemical_formula_sum            'C27 H24 N4'
_chemical_formula_weight         404.50
_chemical_name_systematic
;
N-(2-Aminobenzyl)-N,N-bis(quinolin-2-ylmethyl)amine
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 98.041(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4071(16)
_cell_length_b                   7.9834(10)
_cell_length_c                   21.376(3)
_cell_measurement_reflns_used    3239
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      53.825
_cell_measurement_theta_min      5.454
_cell_volume                     2096.5(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction
'SAINT (Bruker, 2002) and XPREP (Bruker, 2001)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  X-SEED
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0578
_diffrn_reflns_av_sigmaI/netI    0.0712
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14852
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent needle'
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.233
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0574
_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)+(0.0569P)²+0.5447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1342
_reflns_number_gt                3089
_reflns_number_total             4699
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3012.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (4
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (3 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (4
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (3 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2015576
_cod_database_fobs_code          2015576
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
N N1 0.31203(14) 0.81463(19) 0.17491(7) 0.0167(4) Uani d . 1
N N2 0.38292(14) 1.1433(2) 0.07494(8) 0.0177(4) Uani d . 1
N N3 0.15326(14) 0.5904(2) 0.12313(7) 0.0178(4) Uani d . 1
N N4 0.37564(16) 0.4398(2) 0.16790(9) 0.0232(4) Uani d . 1
C C1 0.38390(18) 0.9509(2) 0.16202(9) 0.0181(5) Uani d . 1
H H1A 0.4602 0.9206 0.1780 0.022 Uiso calc R 1
H H1B 0.3653 1.0530 0.1845 0.022 Uiso calc R 1
C C2 0.37363(17) 0.9863(2) 0.09240(9) 0.0176(5) Uani d . 1
C C3 0.35704(17) 0.8517(2) 0.04863(9) 0.0200(5) Uani d . 1
H H3 0.3491 0.7403 0.0630 0.024 Uiso calc R 1
C C4 0.35267(17) 0.8846(2) -0.01413(10) 0.0193(5) Uani d . 1
H H4 0.3431 0.7957 -0.0439 0.023 Uiso calc R 1
C C5 0.36232(16) 1.0511(2) -0.03495(9) 0.0176(5) Uani d . 1
C C6 0.35938(17) 1.0952(3) -0.09919(10) 0.0213(5) Uani d . 1
H H6 0.3494 1.0105 -0.1307 0.026 Uiso calc R 1
C C7 0.37071(18) 1.2578(3) -0.11648(10) 0.0226(5) Uani d . 1
H H7 0.3684 1.2862 -0.1598 0.027 Uiso calc R 1
C C8 0.38581(18) 1.3835(3) -0.06998(10) 0.0233(5) Uani d . 1
H H8 0.3940 1.4967 -0.0823 0.028 Uiso calc R 1
C C9 0.38884(18) 1.3458(2) -0.00765(10) 0.0212(5) Uani d . 1
H H9 0.3983 1.4325 0.0231 0.025 Uiso calc R 1
C C10 0.37789(16) 1.1778(2) 0.01157(9) 0.0181(5) Uani d . 1
C C11 0.19838(17) 0.8672(2) 0.16677(9) 0.0175(5) Uani d . 1
H H11A 0.1907 0.9682 0.1396 0.021 Uiso calc R 1
H H11B 0.1793 0.8996 0.2086 0.021 Uiso calc R 1
C C12 0.11772(17) 0.7377(2) 0.13815(9) 0.0176(5) Uani d . 1
C C13 0.00605(18) 0.7839(3) 0.12818(10) 0.0209(5) Uani d . 1
H H13 -0.0160 0.8912 0.1408 0.025 Uiso calc R 1
C C14 -0.06876(18) 0.6731(3) 0.10046(10) 0.0232(5) Uani d . 1
H H14 -0.1436 0.7028 0.0931 0.028 Uiso calc R 1
C C15 -0.03476(18) 0.5131(2) 0.08251(9) 0.0192(5) Uani d . 1
C C16 -0.10710(18) 0.3892(3) 0.05350(10) 0.0234(5) Uani d . 1
H H16 -0.1826 0.4134 0.0438 0.028 Uiso calc R 1
C C17 -0.06929(19) 0.2366(3) 0.03951(10) 0.0239(5) Uani d . 1
H H17 -0.1185 0.1539 0.0207 0.029 Uiso calc R 1
C C18 0.04253(18) 0.1998(3) 0.05268(10) 0.0231(5) Uani d . 1
H H18 0.0682 0.0924 0.0425 0.028 Uiso calc R 1
C C19 0.11492(18) 0.3178(2) 0.08011(9) 0.0193(5) Uani d . 1
H H19 0.1903 0.2919 0.0885 0.023 Uiso calc R 1
C C20 0.07766(17) 0.4762(2) 0.09564(9) 0.0184(5) Uani d . 1
C C21 0.34498(17) 0.7398(2) 0.23747(9) 0.0185(5) Uani d . 1
H H21A 0.2882 0.6599 0.2465 0.022 Uiso calc R 1
H H21B 0.3500 0.8293 0.2698 0.022 Uiso calc R 1
C C22 0.45217(18) 0.6499(2) 0.24264(9) 0.0185(5) Uani d . 1
C C23 0.46258(18) 0.5027(2) 0.20754(9) 0.0193(5) Uani d . 1
C C24 0.56236(18) 0.4168(3) 0.21622(10) 0.0218(5) Uani d . 1
H H24 0.5696 0.3157 0.1937 0.026 Uiso calc R 1
C C25 0.65032(19) 0.4772(3) 0.25708(10) 0.0244(5) Uani d . 1
H H25 0.7176 0.4185 0.2619 0.029 Uiso calc R 1
C C26 0.64041(18) 0.6235(3) 0.29100(10) 0.0231(5) Uani d . 1
H H26 0.7004 0.6652 0.3192 0.028 Uiso calc R 1
C C27 0.54226(18) 0.7071(3) 0.28319(10) 0.0219(5) Uani d . 1
H H27 0.5359 0.8074 0.3063 0.026 Uiso calc R 1
H H4A 0.383(2) 0.344(3) 0.1418(13) 0.050(8) Uiso d . 1
H H4B 0.321(2) 0.519(3) 0.1520(12) 0.045(8) Uiso d . 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
_geom_angle_publ_flag
C1 N1 C11 111.7(2) y
C1 N1 C21 112.1(2) y
C11 N1 C21 111.5(2) y
C2 N2 C10 118.43(17) ?
C12 N3 C20 117.73(18) ?
C23 N4 H4A 121.1(16) ?
C23 N4 H4B 115.9(15) ?
H4A N4 H4B 116(2) ?
N1 C1 C2 111.00(16) ?
N1 C1 H1A 109.4 ?
C2 C1 H1A 109.4 ?
N1 C1 H1B 109.4 ?
C2 C1 H1B 109.4 ?
H1A C1 H1B 108.0 ?
N2 C2 C3 122.90(18) ?
N2 C2 C1 117.44(17) ?
C3 C2 C1 119.64(17) ?
C4 C3 C2 119.03(18) ?
C4 C3 H3 120.5 ?
C2 C3 H3 120.5 ?
C3 C4 C5 119.94(18) ?
C3 C4 H4 120.0 ?
C5 C4 H4 120.0 ?
C4 C5 C10 117.47(18) ?
C4 C5 C6 123.30(19) ?
C10 C5 C6 119.22(18) ?
C7 C6 C5 120.77(19) ?
C7 C6 H6 119.6 ?
C5 C6 H6 119.6 ?
C6 C7 C8 119.78(19) ?
C6 C7 H7 120.1 ?
C8 C7 H7 120.1 ?
C9 C8 C7 121.09(19) ?
C9 C8 H8 119.5 ?
C7 C8 H8 119.5 ?
C8 C9 C10 120.22(19) ?
C8 C9 H9 119.9 ?
C10 C9 H9 119.9 ?
N2 C10 C5 122.21(18) ?
N2 C10 C9 118.88(18) ?
C5 C10 C9 118.91(18) ?
N1 C11 C12 115.26(16) ?
N1 C11 H11A 108.5 ?
C12 C11 H11A 108.5 ?
N1 C11 H11B 108.5 ?
C12 C11 H11B 108.5 ?
H11A C11 H11B 107.5 ?
N3 C12 C13 123.39(19) ?
N3 C12 C11 119.17(19) ?
C13 C12 C11 117.43(18) ?
C14 C13 C12 119.30(19) ?
C14 C13 H13 120.3 ?
C12 C13 H13 120.3 ?
C13 C14 C15 119.7(2) ?
C13 C14 H14 120.2 ?
C15 C14 H14 120.2 ?
C20 C15 C14 117.20(19) ?
C20 C15 C16 119.18(19) ?
C14 C15 C16 123.6(2) ?
C17 C16 C15 120.4(2) ?
C17 C16 H16 119.8 ?
C15 C16 H16 119.8 ?
C16 C17 C18 120.4(2) ?
C16 C17 H17 119.8 ?
C18 C17 H17 119.8 ?
C19 C18 C17 120.6(2) ?
C19 C18 H18 119.7 ?
C17 C18 H18 119.7 ?
C18 C19 C20 120.1(2) ?
C18 C19 H19 119.9 ?
C20 C19 H19 119.9 ?
N3 C20 C19 118.05(19) ?
N3 C20 C15 122.67(18) ?
C19 C20 C15 119.28(19) ?
N1 C21 C22 113.08(16) ?
N1 C21 H21A 109.0 ?
C22 C21 H21A 109.0 ?
N1 C21 H21B 109.0 ?
C22 C21 H21B 109.0 ?
H21A C21 H21B 107.8 ?
C27 C22 C23 118.6(2) ?
C27 C22 C21 120.98(18) ?
C23 C22 C21 120.35(18) ?
N4 C23 C24 120.37(19) ?
N4 C23 C22 120.8(2) ?
C24 C23 C22 118.78(19) ?
C25 C24 C23 121.0(2) ?
C25 C24 H24 119.5 ?
C23 C24 H24 119.5 ?
C24 C25 C26 120.2(2) ?
C24 C25 H25 119.9 ?
C26 C25 H25 119.9 ?
C27 C26 C25 119.0(2) ?
C27 C26 H26 120.5 ?
C25 C26 H26 120.5 ?
C26 C27 C22 122.36(19) ?
C26 C27 H27 118.8 ?
C22 C27 H27 118.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 1.457(3) y
N1 C11 1.458(3) y
N1 C21 1.469(2) y
N2 C2 1.317(2) ?
N2 C10 1.375(3) ?
N3 C12 1.311(3) ?
N3 C20 1.379(3) ?
N4 C23 1.370(3) y
N4 H4A 0.96(3) ?
N4 H4B 0.95(3) ?
C1 C2 1.502(3) ?
C1 H1A 0.9900 ?
C1 H1B 0.9900 ?
C2 C3 1.421(3) ?
C3 C4 1.361(3) ?
C3 H3 0.9500 ?
C4 C5 1.412(3) ?
C4 H4 0.9500 ?
C5 C10 1.412(3) ?
C5 C6 1.413(3) ?
C6 C7 1.362(3) ?
C6 H6 0.9500 ?
C7 C8 1.407(3) ?
C7 H7 0.9500 ?
C8 C9 1.362(3) ?
C8 H8 0.9500 ?
C9 C10 1.415(3) ?
C9 H9 0.9500 ?
C11 C12 1.508(3) ?
C11 H11A 0.9900 ?
C11 H11B 0.9900 ?
C12 C13 1.421(3) ?
C13 C14 1.357(3) ?
C13 H13 0.9500 ?
C14 C15 1.415(3) ?
C14 H14 0.9500 ?
C15 C20 1.415(3) ?
C15 C16 1.419(3) ?
C16 C17 1.354(3) ?
C16 H16 0.9500 ?
C17 C18 1.408(3) ?
C17 H17 0.9500 ?
C18 C19 1.375(3) ?
C18 H18 0.9500 ?
C19 C20 1.402(3) ?
C19 H19 0.9500 ?
C21 C22 1.502(3) ?
C21 H21A 0.9900 ?
C21 H21B 0.9900 ?
C22 C27 1.392(3) ?
C22 C23 1.410(3) ?
C23 C24 1.405(3) ?
C24 C25 1.386(3) ?
C24 H24 0.9500 ?
C25 C26 1.389(3) ?
C25 H25 0.9500 ?
C26 C27 1.378(3) ?
C26 H26 0.9500 ?
C27 H27 0.9500 ?
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
N4 H4B N3 . 0.95(3) 2.17(3) 3.039(3) 152(2)
N4 H4B N1 . 0.95(3) 2.42(3) 3.104(3) 129(2)
N4 H4A N2 1_545 0.96(3) 2.15(3) 3.100(2) 172(2)
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
C11 N1 C1 C2 -73.2(2)
C21 N1 C1 C2 160.86(16)
C10 N2 C2 C3 -1.0(3)
C10 N2 C2 C1 177.59(18)
N1 C1 C2 N2 145.02(19)
N1 C1 C2 C3 -36.4(3)
N2 C2 C3 C4 1.4(3)
C1 C2 C3 C4 -177.1(2)
C2 C3 C4 C5 -1.3(3)
C3 C4 C5 C10 0.9(3)
C3 C4 C5 C6 179.5(2)
C4 C5 C6 C7 -179.0(2)
C10 C5 C6 C7 -0.4(3)
C5 C6 C7 C8 0.2(3)
C6 C7 C8 C9 -0.3(3)
C7 C8 C9 C10 0.7(3)
C2 N2 C10 C5 0.5(3)
C2 N2 C10 C9 -179.39(19)
C4 C5 C10 N2 -0.5(3)
C6 C5 C10 N2 -179.18(19)
C4 C5 C10 C9 179.45(19)
C6 C5 C10 C9 0.7(3)
C8 C9 C10 N2 179.0(2)
C8 C9 C10 C5 -0.9(3)
C1 N1 C11 C12 142.47(17)
C21 N1 C11 C12 -91.2(2)
C20 N3 C12 C13 0.7(3)
C20 N3 C12 C11 -178.46(17)
N1 C11 C12 N3 0.3(3)
N1 C11 C12 C13 -178.89(17)
N3 C12 C13 C14 -1.5(3)
C11 C12 C13 C14 177.66(19)
C12 C13 C14 C15 0.6(3)
C13 C14 C15 C20 0.9(3)
C13 C14 C15 C16 179.8(2)
C20 C15 C16 C17 1.1(3)
C14 C15 C16 C17 -177.8(2)
C15 C16 C17 C18 -1.0(3)
C16 C17 C18 C19 0.2(3)
C17 C18 C19 C20 0.4(3)
C12 N3 C20 C19 -179.28(18)
C12 N3 C20 C15 0.9(3)
C18 C19 C20 N3 179.93(18)
C18 C19 C20 C15 -0.3(3)
C14 C15 C20 N3 -1.7(3)
C16 C15 C20 N3 179.31(18)
C14 C15 C20 C19 178.49(18)
C16 C15 C20 C19 -0.5(3)
C1 N1 C21 C22 -66.8(2)
C11 N1 C21 C22 167.12(16)
N1 C21 C22 C27 114.6(2)
N1 C21 C22 C23 -67.1(2)
C27 C22 C23 N4 178.78(19)
C21 C22 C23 N4 0.4(3)
C27 C22 C23 C24 1.9(3)
C21 C22 C23 C24 -176.47(18)
N4 C23 C24 C25 -178.7(2)
C22 C23 C24 C25 -1.8(3)
C23 C24 C25 C26 1.0(3)
C24 C25 C26 C27 -0.2(3)
C25 C26 C27 C22 0.3(3)
C23 C22 C27 C26 -1.2(3)
C21 C22 C27 C26 177.18(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133424
