#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/27/7202708.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_7202708
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            'C20 H20 N2 O3'
_chemical_formula_weight         336.38
_chemical_name_systematic
;

?

;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.11390(10)
_cell_length_b                   13.4807(3)
_cell_length_c                   24.8362(5)
_cell_measurement_reflns_used    2214
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.98
_cell_measurement_theta_min      2.89
_cell_volume                     1712.18(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            18583
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.0(14)
_refine_ls_extinction_coef       0.0027(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0501
_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)+(0.0419P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                2329
_reflns_number_total             4201
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b700701a.txt
_cod_data_source_block           quinmpea_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7202708
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 0.5401(5) 0.85863(18) 0.28605(9) 0.0621(6) Uani 1 1 d . . .
H1 H 0.6279 0.7996 0.2931 0.075 Uiso 1 1 calc R . .
C2 C 0.6096(5) 0.9425(2) 0.31608(10) 0.0709(7) Uani 1 1 d . . .
H2 H 0.7402 0.9386 0.3420 0.085 Uiso 1 1 calc R . .
C3 C 0.4855(6) 1.02869(19) 0.30693(10) 0.0664(7) Uani 1 1 d . . .
H3 H 0.5303 1.0851 0.3264 0.080 Uiso 1 1 calc R . .
C4 C 0.2875(5) 1.03323(16) 0.26772(9) 0.0518(6) Uani 1 1 d . . .
C5 C 0.2323(5) 0.94469(15) 0.23896(8) 0.0453(5) Uani 1 1 d . . .
C6 C 0.1451(6) 1.12012(18) 0.25671(10) 0.0686(8) Uani 1 1 d . . .
H6 H 0.1816 1.1782 0.2755 0.082 Uiso 1 1 calc R . .
C7 C -0.0466(6) 1.11946(17) 0.21852(10) 0.0691(7) Uani 1 1 d . . .
H7 H -0.1419 1.1770 0.2121 0.083 Uiso 1 1 calc R . .
C8 C -0.1027(5) 1.03313(16) 0.18870(10) 0.0600(7) Uani 1 1 d . . .
H8 H -0.2321 1.0343 0.1624 0.072 Uiso 1 1 calc R . .
C9 C 0.0326(4) 0.94813(15) 0.19848(8) 0.0469(5) Uani 1 1 d . . .
C10 C -0.2302(4) 0.85498(15) 0.13757(8) 0.0530(6) Uani 1 1 d . . .
H10A H -0.2191 0.9060 0.1101 0.064 Uiso 1 1 calc R . .
H10B H -0.3863 0.8670 0.1588 0.064 Uiso 1 1 calc R . .
C11 C -0.2487(5) 0.75478(15) 0.11118(8) 0.0455(5) Uani 1 1 d . . .
C12 C -0.0171(5) 0.61043(15) 0.07619(8) 0.0538(6) Uani 1 1 d . . .
H12A H -0.1853 0.5779 0.0797 0.065 Uiso 1 1 calc R . .
H12B H 0.1127 0.5689 0.0936 0.065 Uiso 1 1 calc R . .
C13 C 0.0496(5) 0.62013(15) 0.01749(8) 0.0646(7) Uani 1 1 d . . .
H13A H 0.2168 0.6535 0.0141 0.077 Uiso 1 1 calc R . .
H13B H -0.0813 0.6612 0.0001 0.077 Uiso 1 1 calc R . .
C14 C 0.0636(5) 0.52135(16) -0.01133(8) 0.0515(6) Uani 1 1 d . . .
C15 C 0.2549(5) 0.45247(18) 0.00089(9) 0.0610(6) Uani 1 1 d . . .
H15 H 0.3740 0.4667 0.0281 0.073 Uiso 1 1 calc R . .
C16 C 0.2747(5) 0.36265(17) -0.02615(9) 0.0601(6) Uani 1 1 d . . .
H16 H 0.4058 0.3179 -0.0171 0.072 Uiso 1 1 calc R . .
C17 C 0.1006(5) 0.34019(17) -0.06624(9) 0.0522(6) Uani 1 1 d . . .
C18 C -0.0931(5) 0.40734(18) -0.07871(9) 0.0597(7) Uani 1 1 d . . .
H18 H -0.2128 0.3926 -0.1057 0.072 Uiso 1 1 calc R . .
C19 C -0.1115(5) 0.49630(17) -0.05153(9) 0.0582(6) Uani 1 1 d . . .
H19 H -0.2445 0.5404 -0.0604 0.070 Uiso 1 1 calc R . .
C20 C 0.3132(6) 0.18791(19) -0.08803(11) 0.0896(9) Uani 1 1 d . . .
H20A H 0.4750 0.2207 -0.0963 0.134 Uiso 1 1 calc R . .
H20B H 0.2921 0.1315 -0.1112 0.134 Uiso 1 1 calc R . .
H20C H 0.3151 0.1664 -0.0512 0.134 Uiso 1 1 calc R . .
H2N H 0.117(6) 0.7329(17) 0.1128(10) 0.082(9) Uiso 1 1 d . . .
N1 N 0.3587(4) 0.85782(13) 0.24842(7) 0.0524(5) Uani 1 1 d . . .
N2 N -0.0273(4) 0.70594(14) 0.10364(7) 0.0508(5) Uani 1 1 d . . .
O1 O -0.0063(3) 0.86000(10) 0.17140(5) 0.0549(4) Uani 1 1 d . . .
O2 O -0.4625(3) 0.72432(12) 0.09652(7) 0.0659(5) Uani 1 1 d . . .
O3 O 0.1021(4) 0.25477(13) -0.09607(7) 0.0754(5) 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 124.3(2) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C6 C4 C3 122.9(2) . . ?
C6 C4 C5 120.0(2) . . ?
C3 C4 C5 117.1(2) . . ?
N1 C5 C4 122.9(2) . . ?
N1 C5 C9 119.22(18) . . ?
C4 C5 C9 117.9(2) . . ?
C7 C6 C4 120.1(2) . . ?
C7 C6 H6 119.9 . . ?
C4 C6 H6 119.9 . . ?
C6 C7 C8 121.2(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 119.9(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 O1 124.4(2) . . ?
C8 C9 C5 120.98(19) . . ?
O1 C9 C5 114.62(18) . . ?
O1 C10 C11 110.54(17) . . ?
O1 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O2 C11 N2 123.8(2) . . ?
O2 C11 C10 119.2(2) . . ?
N2 C11 C10 117.0(2) . . ?
N2 C12 C13 112.64(17) . . ?
N2 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N2 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C14 113.14(18) . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C19 C14 C15 116.9(2) . . ?
C19 C14 C13 121.7(2) . . ?
C15 C14 C13 121.4(2) . . ?
C14 C15 C16 122.1(2) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 O3 125.1(2) . . ?
C16 C17 C18 119.1(2) . . ?
O3 C17 C18 115.8(2) . . ?
C17 C18 C19 120.7(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 121.4(2) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C5 116.80(19) . . ?
C11 N2 C12 122.4(2) . . ?
C11 N2 H2N 119.3(16) . . ?
C12 N2 H2N 118.1(17) . . ?
C9 O1 C10 116.44(17) . . ?
C17 O3 C20 117.52(19) . . ?
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(3) . ?
C1 C2 1.401(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.343(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.406(3) . ?
C3 H3 0.9300 . ?
C4 C6 1.406(3) . ?
C4 C5 1.419(3) . ?
C5 N1 1.358(3) . ?
C5 C9 1.434(3) . ?
C6 C7 1.364(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.409(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.360(3) . ?
C8 H8 0.9300 . ?
C9 O1 1.380(2) . ?
C10 O1 1.421(2) . ?
C10 C11 1.504(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O2 1.224(2) . ?
C11 N2 1.323(3) . ?
C12 N2 1.458(3) . ?
C12 C13 1.503(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.513(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.383(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.388(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(3) . ?
C16 H16 0.9300 . ?
C17 O3 1.369(3) . ?
C17 C18 1.377(3) . ?
C18 C19 1.379(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 O3 1.420(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N2 H2N 0.85(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 0.3(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C6 178.6(2) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C6 C4 C5 N1 -178.6(2) . . . . ?
C3 C4 C5 N1 0.9(3) . . . . ?
C6 C4 C5 C9 1.0(3) . . . . ?
C3 C4 C5 C9 -179.4(2) . . . . ?
C3 C4 C6 C7 -179.3(2) . . . . ?
C5 C4 C6 C7 0.2(3) . . . . ?
C4 C6 C7 C8 -1.2(4) . . . . ?
C6 C7 C8 C9 1.1(4) . . . . ?
C7 C8 C9 O1 -179.6(2) . . . . ?
C7 C8 C9 C5 0.2(3) . . . . ?
N1 C5 C9 C8 178.4(2) . . . . ?
C4 C5 C9 C8 -1.2(3) . . . . ?
N1 C5 C9 O1 -1.7(3) . . . . ?
C4 C5 C9 O1 178.63(19) . . . . ?
O1 C10 C11 O2 154.92(19) . . . . ?
O1 C10 C11 N2 -27.3(3) . . . . ?
N2 C12 C13 C14 179.4(2) . . . . ?
C12 C13 C14 C19 114.6(2) . . . . ?
C12 C13 C14 C15 -66.3(3) . . . . ?
C19 C14 C15 C16 0.9(3) . . . . ?
C13 C14 C15 C16 -178.2(2) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C15 C16 C17 O3 179.2(2) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
O3 C17 C18 C19 -179.4(2) . . . . ?
C17 C18 C19 C14 0.4(4) . . . . ?
C15 C14 C19 C18 -1.0(3) . . . . ?
C13 C14 C19 C18 178.1(2) . . . . ?
C2 C1 N1 C5 -0.3(3) . . . . ?
C4 C5 N1 C1 -0.3(3) . . . . ?
C9 C5 N1 C1 -179.93(19) . . . . ?
O2 C11 N2 C12 0.7(3) . . . . ?
C10 C11 N2 C12 -176.95(18) . . . . ?
C13 C12 N2 C11 96.0(3) . . . . ?
C8 C9 O1 C10 -10.5(3) . . . . ?
C5 C9 O1 C10 169.70(17) . . . . ?
C11 C10 O1 C9 -179.49(17) . . . . ?
C16 C17 O3 C20 -5.6(3) . . . . ?
C18 C17 O3 C20 174.1(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 6201400
