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#$Date: 2016-03-26 16:50:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180358 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/27/7202706.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_7202706
loop_
_publ_author_name
'Karmakar, Anirban'
'Sarma, Rupam J.'
'Baruah, Jubaraj B.'
_publ_section_title
;
 Structural aspects and properties of salt and inclusion compounds of
 8-hydroxyquinoline based amides
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              379
_journal_paper_doi               10.1039/b700701a
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C44 H42 N4 O6'
_chemical_formula_weight         722.82
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_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                114.290(4)
_cell_angle_beta                 99.137(4)
_cell_angle_gamma                96.136(4)
_cell_formula_units_Z            1
_cell_length_a                   7.528(2)
_cell_length_b                   11.516(3)
_cell_length_c                   12.334(3)
_cell_measurement_temperature    296(2)
_cell_volume                     944.5(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8512
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         7.61
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             382
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.025
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0456
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1604
_reflns_number_gt                2845
_reflns_number_total             4332
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b700701a.txt
_cod_data_source_block           dmahq
_cod_original_cell_volume        944.4(4)
_cod_database_code               7202706
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3093(2) 0.96285(15) 0.79988(15) 0.0578(4) Uani 1 1 d . . .
H1 H 0.3292 0.9340 0.7213 0.069 Uiso 1 1 calc R . .
C2 C 0.3056(3) 1.09456(15) 0.86397(19) 0.0650(5) Uani 1 1 d . . .
H2 H 0.3242 1.1514 0.8290 0.078 Uiso 1 1 calc R . .
C3 C 0.2747(2) 1.13718(14) 0.97649(18) 0.0629(5) Uani 1 1 d . . .
H3 H 0.2704 1.2243 1.0200 0.075 Uiso 1 1 calc R . .
C4 C 0.2488(2) 1.05089(13) 1.02955(15) 0.0518(4) Uani 1 1 d . . .
C5 C 0.25724(18) 0.91926(12) 0.95874(12) 0.0438(3) Uani 1 1 d . . .
C6 C 0.2173(2) 1.08908(15) 1.14757(16) 0.0651(5) Uani 1 1 d . . .
H6 H 0.2122 1.1753 1.1946 0.078 Uiso 1 1 calc R . .
C7 C 0.1944(3) 1.00181(18) 1.19289(16) 0.0674(5) Uani 1 1 d . . .
H7 H 0.1710 1.0283 1.2705 0.081 Uiso 1 1 calc R . .
C8 C 0.2052(2) 0.87052(16) 1.12487(14) 0.0592(4) Uani 1 1 d . . .
H8 H 0.1909 0.8119 1.1583 0.071 Uiso 1 1 calc R . .
C9 C 0.2367(2) 0.82983(12) 1.00999(13) 0.0466(3) Uani 1 1 d . . .
C10 C 0.2484(3) 0.61646(14) 0.98924(15) 0.0591(4) Uani 1 1 d . . .
H10A H 0.1285 0.6023 1.0062 0.071 Uiso 1 1 calc R . .
H10B H 0.3386 0.6526 1.0659 0.071 Uiso 1 1 calc R . .
C11 C 0.2879(3) 0.48843(14) 0.90456(15) 0.0572(4) Uani 1 1 d . . .
C12 C 0.3744(2) 0.36887(13) 0.71104(13) 0.0492(4) Uani 1 1 d . . .
C13 C 0.2456(2) 0.25324(15) 0.64767(15) 0.0597(4) Uani 1 1 d . . .
C14 C 0.2975(3) 0.15085(17) 0.55700(18) 0.0783(6) Uani 1 1 d . . .
H14 H 0.2170 0.0713 0.5158 0.094 Uiso 1 1 calc R . .
C15 C 0.4623(4) 0.16402(19) 0.5272(2) 0.0852(6) Uani 1 1 d . . .
H15 H 0.4915 0.0948 0.4646 0.102 Uiso 1 1 calc R . .
C16 C 0.5855(3) 0.2790(2) 0.58912(18) 0.0734(5) Uani 1 1 d . . .
H16 H 0.6976 0.2873 0.5677 0.088 Uiso 1 1 calc R . .
C17 C 0.5454(2) 0.38317(15) 0.68335(14) 0.0564(4) Uani 1 1 d . . .
C18 C 0.6815(3) 0.50893(19) 0.75195(18) 0.0736(5) Uani 1 1 d . . .
H18A H 0.7964 0.4976 0.7284 0.110 Uiso 1 1 calc R . .
H18B H 0.6988 0.5346 0.8380 0.110 Uiso 1 1 calc R . .
H18C H 0.6362 0.5749 0.7332 0.110 Uiso 1 1 calc R . .
C19 C 0.0586(3) 0.2405(2) 0.6708(2) 0.0881(6) Uani 1 1 d . . .
H19A H 0.0651 0.2371 0.7478 0.132 Uiso 1 1 calc R . .
H19B H -0.0173 0.1623 0.6069 0.132 Uiso 1 1 calc R . .
H19C H 0.0071 0.3139 0.6727 0.132 Uiso 1 1 calc R . .
C21 C 0.1608(3) 0.45342(15) 0.49675(14) 0.0608(4) Uani 1 1 d . . .
H21 H 0.2692 0.4215 0.4942 0.073 Uiso 1 1 calc R . .
C22 C 0.1584(2) 0.57460(14) 0.58747(12) 0.0509(4) Uani 1 1 d . . .
C23 C -0.0030(3) 0.61981(14) 0.58951(14) 0.0590(4) Uani 1 1 d . . .
H23 H -0.0061 0.7009 0.6499 0.071 Uiso 1 1 calc R . .
H2N H 0.337(3) 0.548(2) 0.7867(18) 0.072(6) Uiso 1 1 d . . .
H3O H 0.304(3) 0.717(3) 0.733(2) 0.087(6) Uiso 1 1 d . . .
N1 N 0.28650(17) 0.87709(11) 0.84391(11) 0.0478(3) Uani 1 1 d . . .
N2 N 0.3270(2) 0.47972(12) 0.80023(11) 0.0523(3) Uani 1 1 d . . .
O1 O 0.25293(16) 0.70594(9) 0.93767(9) 0.0545(3) Uani 1 1 d . . .
O2 O 0.2827(2) 0.40073(11) 0.93598(12) 0.0830(5) Uani 1 1 d . . .
O3 O 0.31915(17) 0.64332(11) 0.67208(10) 0.0607(3) Uani 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 124.10(16) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C3 C2 C1 118.67(16) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.41(14) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C6 C4 C3 123.47(14) . . ?
C6 C4 C5 119.33(15) . . ?
C3 C4 C5 117.20(15) . . ?
N1 C5 C4 121.70(13) . . ?
N1 C5 C9 119.28(11) . . ?
C4 C5 C9 119.01(14) . . ?
C7 C6 C4 120.42(14) . . ?
C7 C6 H6 119.8 . . ?
C4 C6 H6 119.8 . . ?
C6 C7 C8 121.29(16) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 119.98(17) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 O1 124.59(14) . . ?
C8 C9 C5 119.93(13) . . ?
O1 C9 C5 115.47(12) . . ?
O1 C10 C11 111.39(13) . . ?
O1 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
O1 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O2 C11 N2 124.56(14) . . ?
O2 C11 C10 118.35(15) . . ?
N2 C11 C10 117.08(13) . . ?
C17 C12 C13 121.86(14) . . ?
C17 C12 N2 118.02(13) . . ?
C13 C12 N2 119.94(15) . . ?
C14 C13 C12 116.96(18) . . ?
C14 C13 C19 120.94(17) . . ?
C12 C13 C19 122.04(16) . . ?
C15 C14 C13 121.88(17) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 120.18(17) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 120.9(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C12 118.17(16) . . ?
C16 C17 C18 120.81(18) . . ?
C12 C17 C18 121.01(15) . . ?
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 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C23 C21 C22 120.24(16) 2_566 . ?
C23 C21 H21 119.9 2_566 . ?
C22 C21 H21 119.9 . . ?
C23 C22 O3 123.12(13) . . ?
C23 C22 C21 118.91(15) . . ?
O3 C22 C21 117.97(15) . . ?
C22 C23 C21 120.85(14) . 2_566 ?
C22 C23 H23 119.6 . . ?
C21 C23 H23 119.6 2_566 . ?
C1 N1 C5 117.92(12) . . ?
C11 N2 C12 125.25(13) . . ?
C11 N2 H2N 119.2(14) . . ?
C12 N2 H2N 115.2(14) . . ?
C9 O1 C10 117.17(12) . . ?
C22 O3 H3O 112.7(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.317(2) . ?
C1 C2 1.399(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.337(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.410(2) . ?
C3 H3 0.9300 . ?
C4 C6 1.405(3) . ?
C4 C5 1.4192(18) . ?
C5 N1 1.3588(19) . ?
C5 C9 1.420(2) . ?
C6 C7 1.345(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.415(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.367(2) . ?
C8 H8 0.9300 . ?
C9 O1 1.3678(16) . ?
C10 O1 1.4164(18) . ?
C10 C11 1.509(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O2 1.2207(19) . ?
C11 N2 1.332(2) . ?
C12 C17 1.393(3) . ?
C12 C13 1.397(2) . ?
C12 N2 1.4260(19) . ?
C13 C14 1.395(3) . ?
C13 C19 1.484(3) . ?
C14 C15 1.360(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.504(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C23 1.378(2) 2_566 ?
C21 C22 1.388(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.372(2) . ?
C22 O3 1.376(2) . ?
C23 C21 1.378(2) 2_566 ?
C23 H23 0.9300 . ?
N2 H2N 0.87(2) . ?
O3 H3O 0.90(3) . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.9(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C6 179.47(17) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C6 C4 C5 N1 179.69(14) . . . . ?
C3 C4 C5 N1 -0.9(2) . . . . ?
C6 C4 C5 C9 -1.1(2) . . . . ?
C3 C4 C5 C9 178.32(13) . . . . ?
C3 C4 C6 C7 -179.70(16) . . . . ?
C5 C4 C6 C7 -0.4(2) . . . . ?
C4 C6 C7 C8 1.4(3) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 O1 178.75(15) . . . . ?
C7 C8 C9 C5 -0.5(2) . . . . ?
N1 C5 C9 C8 -179.28(14) . . . . ?
C4 C5 C9 C8 1.5(2) . . . . ?
N1 C5 C9 O1 1.45(19) . . . . ?
C4 C5 C9 O1 -177.82(12) . . . . ?
O1 C10 C11 O2 -177.74(16) . . . . ?
O1 C10 C11 N2 2.6(2) . . . . ?
C17 C12 C13 C14 1.6(3) . . . . ?
N2 C12 C13 C14 176.54(16) . . . . ?
C17 C12 C13 C19 -175.58(19) . . . . ?
N2 C12 C13 C19 -0.7(3) . . . . ?
C12 C13 C14 C15 -3.0(3) . . . . ?
C19 C13 C14 C15 174.3(2) . . . . ?
C13 C14 C15 C16 2.0(4) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C16 C17 C12 -1.7(3) . . . . ?
C15 C16 C17 C18 179.5(2) . . . . ?
C13 C12 C17 C16 0.6(2) . . . . ?
N2 C12 C17 C16 -174.36(15) . . . . ?
C13 C12 C17 C18 179.43(16) . . . . ?
N2 C12 C17 C18 4.4(2) . . . . ?
C23 C21 C22 C23 -0.1(3) 2_566 . . . ?
C23 C21 C22 O3 179.40(15) 2_566 . . . ?
O3 C22 C23 C21 -179.38(15) . . . 2_566 ?
C21 C22 C23 C21 0.1(3) . . . 2_566 ?
C2 C1 N1 C5 0.1(2) . . . . ?
C4 C5 N1 C1 0.8(2) . . . . ?
C9 C5 N1 C1 -178.42(13) . . . . ?
O2 C11 N2 C12 -2.1(3) . . . . ?
C10 C11 N2 C12 177.60(16) . . . . ?
C17 C12 N2 C11 -119.57(18) . . . . ?
C13 C12 N2 C11 65.3(2) . . . . ?
C8 C9 O1 C10 -4.3(2) . . . . ?
C5 C9 O1 C10 174.94(13) . . . . ?
C11 C10 O1 C9 -173.91(13) . . . . ?
