#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:50:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180358 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/27/7202707.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_7202707
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            'C24 H22 N2 O3'
_chemical_formula_weight         386.44
_chemical_name_systematic
;

?

;
_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                111.239(2)
_cell_angle_beta                 93.668(2)
_cell_angle_gamma                105.441(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1869(2)
_cell_length_b                   10.4020(2)
_cell_length_c                   13.6322(3)
_cell_measurement_reflns_used    1912
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      3.08
_cell_volume                     1026.25(4)
_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 0.853
_diffrn_measured_fraction_theta_max 0.853
_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  0.0153
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5472
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0437
_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)+(0.0536P)²+0.2541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1200
_reflns_number_gt                2684
_reflns_number_total             3430
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b700701a.txt
_cod_data_source_block           dmand_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               7202707
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 0.0560(2) 0.4624(2) 0.19638(17) 0.0629(5) Uani 1 1 d . . .
H1 H 0.0440 0.5088 0.2668 0.075 Uiso 1 1 calc R . .
C2 C -0.0382(2) 0.3153(2) 0.1420(2) 0.0646(6) Uani 1 1 d . . .
H2 H -0.1107 0.2660 0.1754 0.078 Uiso 1 1 calc R . .
C3 C -0.0212(2) 0.24733(18) 0.04056(19) 0.0601(6) Uani 1 1 d . . .
H3 H -0.0822 0.1495 0.0033 0.072 Uiso 1 1 calc R . .
C4 C 0.0879(2) 0.32261(16) -0.01024(16) 0.0487(5) Uani 1 1 d . . .
C5 C 0.17847(19) 0.47191(16) 0.05151(15) 0.0428(4) Uani 1 1 d . . .
C6 C 0.1097(2) 0.25904(19) -0.11614(18) 0.0627(6) Uani 1 1 d . . .
H6 H 0.0494 0.1620 -0.1571 0.075 Uiso 1 1 calc R . .
C7 C 0.2176(3) 0.3374(2) -0.15949(18) 0.0668(6) Uani 1 1 d . . .
H7 H 0.2318 0.2933 -0.2297 0.080 Uiso 1 1 calc R . .
C8 C 0.3093(2) 0.48593(19) -0.09933(16) 0.0570(5) Uani 1 1 d . . .
H8 H 0.3833 0.5382 -0.1303 0.068 Uiso 1 1 calc R . .
C9 C 0.2898(2) 0.55236(16) 0.00305(14) 0.0437(4) Uani 1 1 d . . .
C10 C 0.4847(2) 0.77834(17) 0.02234(14) 0.0472(4) Uani 1 1 d . . .
H10A H 0.4221 0.7770 -0.0411 0.057 Uiso 1 1 calc R . .
H10B H 0.5738 0.7339 0.0008 0.057 Uiso 1 1 calc R . .
C11 C 0.5674(2) 0.93381(17) 0.10055(15) 0.0467(4) Uani 1 1 d . . .
C12 C 0.5736(2) 1.12854(17) 0.26810(15) 0.0493(4) Uani 1 1 d . . .
C13 C 0.7314(2) 1.17649(18) 0.33533(16) 0.0564(5) Uani 1 1 d . . .
C14 C 0.7884(3) 1.3200(2) 0.40879(19) 0.0763(7) Uani 1 1 d . . .
H14 H 0.8936 1.3546 0.4546 0.092 Uiso 1 1 calc R . .
C15 C 0.6923(4) 1.4111(2) 0.4148(2) 0.0892(8) Uani 1 1 d . . .
H15 H 0.7327 1.5067 0.4643 0.107 Uiso 1 1 calc R . .
C16 C 0.5363(4) 1.3620(2) 0.3479(2) 0.0820(7) Uani 1 1 d . . .
H16 H 0.4724 1.4251 0.3523 0.098 Uiso 1 1 calc R . .
C17 C 0.4728(3) 1.2186(2) 0.27332(17) 0.0605(5) Uani 1 1 d . . .
C18 C 0.2998(3) 1.1632(3) 0.2034(2) 0.0865(7) Uani 1 1 d . . .
H18A H 0.2217 1.0948 0.2242 0.130 Uiso 1 1 calc R . .
H18B H 0.3102 1.1163 0.1302 0.130 Uiso 1 1 calc R . .
H18C H 0.2565 1.2428 0.2110 0.130 Uiso 1 1 calc R . .
C19 C 0.8374(3) 1.0788(2) 0.3314(2) 0.0766(7) Uani 1 1 d . . .
H19A H 0.7657 0.9887 0.3306 0.115 Uiso 1 1 calc R . .
H19B H 0.9272 1.1243 0.3933 0.115 Uiso 1 1 calc R . .
H19C H 0.8875 1.0606 0.2679 0.115 Uiso 1 1 calc R . .
C20 C 0.4840(3) 0.7543(2) 0.36385(17) 0.0628(5) Uani 1 1 d . . .
H20 H 0.4565 0.6661 0.3053 0.075 Uiso 1 1 calc R . .
C21 C 0.3913(2) 0.84633(18) 0.36966(14) 0.0495(4) Uani 1 1 d . . .
C22 C 0.4301(2) 0.98156(18) 0.45890(14) 0.0483(4) Uani 1 1 d . . .
C23 C 0.3342(3) 1.0782(2) 0.46739(16) 0.0579(5) Uani 1 1 d . . .
H23 H 0.2410 1.0538 0.4142 0.070 Uiso 1 1 calc R . .
C24 C 0.3777(3) 1.2073(2) 0.55325(18) 0.0693(6) Uani 1 1 d . . .
H24 H 0.3152 1.2712 0.5573 0.083 Uiso 1 1 calc R . .
H2N H 0.425(2) 0.923(2) 0.2032(15) 0.058(5) Uiso 1 1 d . . .
H3O H 0.232(3) 0.719(3) 0.239(2) 0.107(9) Uiso 1 1 d . . .
N1 N 0.16047(18) 0.53911(15) 0.15398(12) 0.0506(4) Uani 1 1 d . . .
N2 N 0.50916(19) 0.98015(15) 0.19147(13) 0.0509(4) Uani 1 1 d . . .
O1 O 0.36951(14) 0.69597(11) 0.06776(9) 0.0481(3) Uani 1 1 d . . .
O2 O 0.68300(17) 1.01016(13) 0.07456(11) 0.0690(4) Uani 1 1 d . . .
O3 O 0.26046(17) 0.81937(14) 0.29053(11) 0.0602(4) 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 124.1(2) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C3 C2 C1 118.42(18) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 120.72(16) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C6 C4 C3 123.70(16) . . ?
C6 C4 C5 119.48(16) . . ?
C3 C4 C5 116.81(18) . . ?
N1 C5 C4 121.83(15) . . ?
N1 C5 C9 119.51(14) . . ?
C4 C5 C9 118.66(17) . . ?
C7 C6 C4 120.55(16) . . ?
C7 C6 H6 119.7 . . ?
C4 C6 H6 119.7 . . ?
C6 C7 C8 120.9(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 120.48(18) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 O1 125.32(15) . . ?
C8 C9 C5 119.96(15) . . ?
O1 C9 C5 114.72(15) . . ?
O1 C10 C11 111.71(14) . . ?
O1 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
O1 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
O2 C11 N2 124.02(15) . . ?
O2 C11 C10 117.29(16) . . ?
N2 C11 C10 118.68(13) . . ?
C13 C12 C17 122.12(16) . . ?
C13 C12 N2 119.58(16) . . ?
C17 C12 N2 118.29(17) . . ?
C12 C13 C14 117.84(19) . . ?
C12 C13 C19 122.05(16) . . ?
C14 C13 C19 120.11(19) . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 120.7(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C12 C17 C16 117.8(2) . . ?
C12 C17 C18 121.30(18) . . ?
C16 C17 C18 120.9(2) . . ?
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 . . ?
C21 C20 C24 119.79(18) . 2_676 ?
C21 C20 H20 120.1 . . ?
C24 C20 H20 120.1 2_676 . ?
C20 C21 O3 123.10(17) . . ?
C20 C21 C22 121.15(17) . . ?
O3 C21 C22 115.71(16) . . ?
C23 C22 C22 119.6(2) . 2_676 ?
C23 C22 C21 122.19(17) . . ?
C22 C22 C21 118.2(2) 2_676 . ?
C24 C23 C22 120.16(19) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C20 121.1(2) . 2_676 ?
C23 C24 H24 119.5 . . ?
C20 C24 H24 119.5 2_676 . ?
C1 N1 C5 118.17(15) . . ?
C11 N2 C12 122.56(14) . . ?
C11 N2 H2N 119.3(13) . . ?
C12 N2 H2N 118.0(13) . . ?
C9 O1 C10 115.99(13) . . ?
C21 O3 H3O 109.6(16) . . ?
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 1.318(2) . ?
C1 C2 1.400(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.342(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.411(3) . ?
C3 H3 0.9300 . ?
C4 C6 1.399(3) . ?
C4 C5 1.425(2) . ?
C5 N1 1.355(2) . ?
C5 C9 1.428(2) . ?
C6 C7 1.351(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.417(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.356(3) . ?
C8 H8 0.9300 . ?
C9 O1 1.3741(18) . ?
C10 O1 1.4270(18) . ?
C10 C11 1.512(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O2 1.2240(19) . ?
C11 N2 1.327(2) . ?
C12 C13 1.390(3) . ?
C12 C17 1.391(3) . ?
C12 N2 1.442(2) . ?
C13 C14 1.391(3) . ?
C13 C19 1.491(3) . ?
C14 C15 1.368(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.497(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.356(3) . ?
C20 C24 1.410(3) 2_676 ?
C20 H20 0.9300 . ?
C21 O3 1.365(2) . ?
C21 C22 1.426(2) . ?
C22 C23 1.410(3) . ?
C22 C22 1.415(4) 2_676 ?
C23 C24 1.361(3) . ?
C23 H23 0.9300 . ?
C24 C20 1.410(3) 2_676 ?
C24 H24 0.9300 . ?
N2 H2N 0.85(2) . ?
O3 H3O 0.98(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 0.2(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C6 -179.05(19) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C6 C4 C5 N1 179.23(16) . . . . ?
C3 C4 C5 N1 -0.3(2) . . . . ?
C6 C4 C5 C9 -0.2(2) . . . . ?
C3 C4 C5 C9 -179.72(15) . . . . ?
C3 C4 C6 C7 -179.48(19) . . . . ?
C5 C4 C6 C7 1.0(3) . . . . ?
C4 C6 C7 C8 -0.8(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 O1 -178.70(18) . . . . ?
C7 C8 C9 C5 1.1(3) . . . . ?
N1 C5 C9 C8 179.71(17) . . . . ?
C4 C5 C9 C8 -0.8(2) . . . . ?
N1 C5 C9 O1 -0.5(2) . . . . ?
C4 C5 C9 O1 178.95(14) . . . . ?
O1 C10 C11 O2 171.97(16) . . . . ?
O1 C10 C11 N2 -9.3(2) . . . . ?
C17 C12 C13 C14 -0.6(3) . . . . ?
N2 C12 C13 C14 -179.43(18) . . . . ?
C17 C12 C13 C19 178.50(19) . . . . ?
N2 C12 C13 C19 -0.3(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C19 C13 C14 C15 -179.2(2) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C13 C12 C17 C16 1.1(3) . . . . ?
N2 C12 C17 C16 179.93(18) . . . . ?
C13 C12 C17 C18 -177.38(19) . . . . ?
N2 C12 C17 C18 1.4(3) . . . . ?
C15 C16 C17 C12 -1.0(3) . . . . ?
C15 C16 C17 C18 177.5(2) . . . . ?
C24 C20 C21 O3 177.17(17) 2_676 . . . ?
C24 C20 C21 C22 -0.5(3) 2_676 . . . ?
C20 C21 C22 C23 -179.20(18) . . . . ?
O3 C21 C22 C23 3.0(2) . . . . ?
C20 C21 C22 C22 0.8(3) . . . 2_676 ?
O3 C21 C22 C22 -177.08(18) . . . 2_676 ?
C22 C22 C23 C24 1.1(3) 2_676 . . . ?
C21 C22 C23 C24 -178.94(18) . . . . ?
C22 C23 C24 C20 -1.4(3) . . . 2_676 ?
C2 C1 N1 C5 -0.1(3) . . . . ?
C4 C5 N1 C1 0.1(3) . . . . ?
C9 C5 N1 C1 179.54(17) . . . . ?
O2 C11 N2 C12 2.1(3) . . . . ?
C10 C11 N2 C12 -176.52(17) . . . . ?
C13 C12 N2 C11 -77.6(2) . . . . ?
C17 C12 N2 C11 103.6(2) . . . . ?
C8 C9 O1 C10 -1.7(2) . . . . ?
C5 C9 O1 C10 178.57(14) . . . . ?
C11 C10 O1 C9 -179.09(14) . . . . ?
