#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/71/2227171.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_2227171
loop_
_publ_author_name
'Rambabu, D.'
'Rama Krishna, G.'
'Malla Reddy, C.'
'Pal, Manojit'
_publ_section_title
;
 4-[(4-Methylbenzyl)amino]-3-[(4-methylbenzyl)iminomethyl]-2H-chromen-2-one
;
_journal_coeditor_code           BH2311
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2870
_journal_paper_doi               10.1107/S1600536810041218
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C26 H24 N2 O2'
_chemical_formula_moiety         'C26 H24 N2 O2'
_chemical_formula_sum            'C26 H24 N2 O2'
_chemical_formula_weight         396.47
_chemical_name_systematic
;
4-[(4-Methylbenzyl)amino]-3-[(4-methylbenzyl)iminomethyl]-2H-chromen-
2-one
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.525(2)
_cell_angle_beta                 97.423(2)
_cell_angle_gamma                107.251(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8137(2)
_cell_length_b                   9.2636(3)
_cell_length_c                   17.4364(5)
_cell_measurement_reflns_used    213
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.36
_cell_volume                     1017.84(6)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD DUO'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17607
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             420.0
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.367
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0630P)²+0.4639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1222
_reflns_number_gt                3867
_reflns_number_total             4391
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            bh2311.cif
_cod_data_source_block           I
_cod_database_code               2227171
_cod_database_fobs_code          2227171
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
O O1 0.71493(13) 0.94920(10) 1.10649(5) 0.0147(2) Uani d . 1 . .
O O2 0.68675(15) 0.70231(11) 1.08127(5) 0.0202(2) Uani d . 1 . .
N N1 0.76368(16) 0.96900(12) 0.87229(6) 0.0135(2) Uani d . 1 . .
N N2 0.70561(15) 0.67083(12) 0.84586(6) 0.0140(2) Uani d . 1 . .
C C1 0.70620(18) 0.81679(14) 1.05335(7) 0.0135(2) Uani d . 1 . .
C C2 0.72049(17) 0.82812(14) 0.97287(7) 0.0121(2) Uani d . 1 . .
C C3 0.75128(17) 0.97000(14) 0.94846(7) 0.0114(2) Uani d . 1 . .
C C4 0.76930(17) 1.10806(14) 1.00772(7) 0.0121(2) Uani d . 1 . .
C C5 0.80667(18) 1.25968(14) 0.99476(8) 0.0149(3) Uani d . 1 . .
H H5 0.8216 1.2774 0.9445 0.018 Uiso calc R 1 . .
C C6 0.82167(19) 1.38246(14) 1.05493(8) 0.0165(3) Uani d . 1 . .
H H6 0.8453 1.4810 1.0447 0.020 Uiso calc R 1 . .
C C7 0.80156(18) 1.35920(15) 1.13092(8) 0.0168(3) Uani d . 1 . .
H H7 0.8122 1.4420 1.1713 0.020 Uiso calc R 1 . .
C C8 0.76572(19) 1.21248(15) 1.14600(7) 0.0160(3) Uani d . 1 . .
H H8 0.7518 1.1961 1.1965 0.019 Uiso calc R 1 . .
C C9 0.75060(17) 1.08969(14) 1.08509(7) 0.0132(2) Uani d . 1 . .
C C10 0.69080(18) 0.68181(14) 0.91907(7) 0.0128(2) Uani d . 1 . .
H H10 0.6596 0.5920 0.9388 0.015 Uiso calc R 1 . .
C C11 0.6554(2) 0.51577(14) 0.79593(8) 0.0169(3) Uani d . 1 . .
H H11A 0.6342 0.4390 0.8284 0.020 Uiso calc R 1 . .
H H11B 0.7703 0.5106 0.7693 0.020 Uiso calc R 1 . .
C C12 0.45765(19) 0.48263(14) 0.73518(7) 0.0150(3) Uani d . 1 . .
C C13 0.2852(2) 0.35067(14) 0.72762(7) 0.0173(3) Uani d . 1 . .
H H13 0.2958 0.2758 0.7560 0.021 Uiso calc R 1 . .
C C14 0.0973(2) 0.33028(15) 0.67797(8) 0.0190(3) Uani d . 1 . .
H H14 -0.0155 0.2411 0.6732 0.023 Uiso calc R 1 . .
C C15 0.0748(2) 0.44085(15) 0.63519(8) 0.0190(3) Uani d . 1 . .
C C16 0.2498(2) 0.57018(15) 0.64110(8) 0.0195(3) Uani d . 1 . .
H H16 0.2401 0.6441 0.6120 0.023 Uiso calc R 1 . .
C C17 0.4385(2) 0.59027(15) 0.68983(8) 0.0177(3) Uani d . 1 . .
H H17 0.5536 0.6766 0.6922 0.021 Uiso calc R 1 . .
C C18 -0.1334(2) 0.42037(19) 0.58467(9) 0.0285(3) Uani d . 1 . .
H H18A -0.1754 0.3258 0.5453 0.043 Uiso calc R 1 . .
H H18B -0.1202 0.5060 0.5591 0.043 Uiso calc R 1 . .
H H18C -0.2368 0.4163 0.6175 0.043 Uiso calc R 1 . .
C C19 0.76994(19) 1.08754(14) 0.82548(7) 0.0147(2) Uani d . 1 . .
H H19A 0.8992 1.1736 0.8443 0.018 Uiso calc R 1 . .
H H19B 0.6536 1.1262 0.8306 0.018 Uiso calc R 1 . .
C C20 0.75631(19) 1.01513(14) 0.73987(7) 0.0145(3) Uani d . 1 . .
C C21 0.9152(2) 0.95875(15) 0.71825(8) 0.0168(3) Uani d . 1 . .
H H21 1.0271 0.9651 0.7568 0.020 Uiso calc R 1 . .
C C22 0.9072(2) 0.89349(15) 0.63983(8) 0.0198(3) Uani d . 1 . .
H H22 1.0138 0.8563 0.6266 0.024 Uiso calc R 1 . .
C C23 0.7413(2) 0.88269(15) 0.58023(8) 0.0200(3) Uani d . 1 . .
C C24 0.5838(2) 0.93895(15) 0.60216(8) 0.0198(3) Uani d . 1 . .
H H24 0.4720 0.9328 0.5636 0.024 Uiso calc R 1 . .
C C25 0.5906(2) 1.00432(15) 0.68088(8) 0.0176(3) Uani d . 1 . .
H H25 0.4836 1.0410 0.6941 0.021 Uiso calc R 1 . .
C C26 0.7341(3) 0.81009(19) 0.49520(9) 0.0309(3) Uani d . 1 . .
H H26A 0.6987 0.7000 0.4891 0.046 Uiso calc R 1 . .
H H26B 0.8686 0.8511 0.4815 0.046 Uiso calc R 1 . .
H H26C 0.6305 0.8331 0.4610 0.046 Uiso calc R 1 . .
H H1 0.751(3) 0.876(2) 0.8455(11) 0.025(4) 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'
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
C9 O1 C1 . . 121.68(10) ?
C3 N1 C19 . . 131.64(11) ?
C3 N1 H1 . . 111.9(12) ?
C19 N1 H1 . . 116.0(12) ?
C10 N2 C11 . . 118.27(11) ?
O2 C1 O1 . . 114.96(11) ?
O2 C1 C2 . . 127.14(11) ?
O1 C1 C2 . . 117.90(10) ?
C3 C2 C1 . . 121.68(11) ?
C3 C2 C10 . . 123.54(11) ?
C1 C2 C10 . . 114.72(11) ?
N1 C3 C2 . . 117.25(11) ?
N1 C3 C4 . . 124.45(11) ?
C2 C3 C4 . . 118.30(11) ?
C9 C4 C5 . . 116.27(11) ?
C9 C4 C3 . . 117.57(11) ?
C5 C4 C3 . . 126.15(11) ?
C6 C5 C4 . . 121.64(12) ?
C6 C5 H5 . . 119.2 ?
C4 C5 H5 . . 119.2 ?
C5 C6 C7 . . 120.29(12) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
C8 C7 C6 . . 119.77(11) ?
C8 C7 H7 . . 120.1 ?
C6 C7 H7 . . 120.1 ?
C7 C8 C9 . . 119.53(12) ?
C7 C8 H8 . . 120.2 ?
C9 C8 H8 . . 120.2 ?
O1 C9 C8 . . 114.75(11) ?
O1 C9 C4 . . 122.75(11) ?
C8 C9 C4 . . 122.50(12) ?
N2 C10 C2 . . 123.26(11) ?
N2 C10 H10 . . 118.4 ?
C2 C10 H10 . . 118.4 ?
N2 C11 C12 . . 108.96(10) ?
N2 C11 H11A . . 109.9 ?
C12 C11 H11A . . 109.9 ?
N2 C11 H11B . . 109.9 ?
C12 C11 H11B . . 109.9 ?
H11A C11 H11B . . 108.3 ?
C13 C12 C17 . . 118.25(12) ?
C13 C12 C11 . . 121.18(11) ?
C17 C12 C11 . . 120.38(11) ?
C14 C13 C12 . . 120.52(12) ?
C14 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
C13 C14 C15 . . 121.40(12) ?
C13 C14 H14 . . 119.3 ?
C15 C14 H14 . . 119.3 ?
C14 C15 C16 . . 117.75(12) ?
C14 C15 C18 . . 120.63(12) ?
C16 C15 C18 . . 121.62(12) ?
C17 C16 C15 . . 121.08(12) ?
C17 C16 H16 . . 119.5 ?
C15 C16 H16 . . 119.5 ?
C16 C17 C12 . . 120.92(12) ?
C16 C17 H17 . . 119.5 ?
C12 C17 H17 . . 119.5 ?
C15 C18 H18A . . 109.5 ?
C15 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C15 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
N1 C19 C20 . . 108.29(10) ?
N1 C19 H19A . . 110.0 ?
C20 C19 H19A . . 110.0 ?
N1 C19 H19B . . 110.0 ?
C20 C19 H19B . . 110.0 ?
H19A C19 H19B . . 108.4 ?
C25 C20 C21 . . 118.50(12) ?
C25 C20 C19 . . 121.85(11) ?
C21 C20 C19 . . 119.65(11) ?
C22 C21 C20 . . 120.64(12) ?
C22 C21 H21 . . 119.7 ?
C20 C21 H21 . . 119.7 ?
C21 C22 C23 . . 121.13(12) ?
C21 C22 H22 . . 119.4 ?
C23 C22 H22 . . 119.4 ?
C24 C23 C22 . . 117.93(12) ?
C24 C23 C26 . . 121.63(13) ?
C22 C23 C26 . . 120.44(13) ?
C23 C24 C25 . . 121.24(12) ?
C23 C24 H24 . . 119.4 ?
C25 C24 H24 . . 119.4 ?
C20 C25 C24 . . 120.57(12) ?
C20 C25 H25 . . 119.7 ?
C24 C25 H25 . . 119.7 ?
C23 C26 H26A . . 109.5 ?
C23 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C23 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 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
O1 C9 . 1.3743(15) ?
O1 C1 . 1.3904(15) ?
O2 C1 . 1.2180(16) ?
N1 C3 . 1.3403(16) ?
N1 C19 . 1.4669(15) ?
N1 H1 . 0.883(19) ?
N2 C10 . 1.2833(16) ?
N2 C11 . 1.4682(15) ?
C1 C2 . 1.4378(17) ?
C2 C3 . 1.4133(16) ?
C2 C10 . 1.4579(16) ?
C3 C4 . 1.4681(16) ?
C4 C9 . 1.4044(17) ?
C4 C5 . 1.4129(17) ?
C5 C6 . 1.3832(18) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.3945(19) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.3835(18) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.3911(17) ?
C8 H8 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C12 . 1.5196(17) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.3955(18) ?
C12 C17 . 1.3956(18) ?
C13 C14 . 1.3928(19) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.3949(19) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.3959(19) ?
C15 C18 . 1.5119(18) ?
C16 C17 . 1.3905(18) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 C20 . 1.5110(17) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 C25 . 1.3934(18) ?
C20 C21 . 1.4008(18) ?
C21 C22 . 1.3877(19) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.4011(19) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.393(2) ?
C23 C26 . 1.5116(19) ?
C24 C25 . 1.3945(19) ?
C24 H24 . 0.9300 ?
C25 H25 . 0.9300 ?
C26 H26A . 0.9600 ?
C26 H26B . 0.9600 ?
C26 H26C . 0.9600 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656178
