#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:52:43 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179544 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/13/4501310.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_4501310
loop_
_publ_author_name
'Kalita, Dipjyoti'
'Baruah, Jubaraj B.'
_publ_section_title
;
 Acid Inclusion Properties of Helical Self-Assembly of a
 5,5′-Biquinoline Derivative
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5131
_journal_paper_doi               10.1021/cg201052k
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C22 H24 Cl2 N4 O10'
_chemical_formula_weight         575.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           70
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-F 2uv 2vw'
_symmetry_space_group_name_H-M   'F d d d :2'
_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            16
_cell_length_a                   51.844(11)
_cell_length_b                   8.1994(19)
_cell_length_c                   24.616(6)
_cell_measurement_reflns_used    1695
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.65
_cell_volume                     10464(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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1218
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       61
_diffrn_reflns_limit_h_min       -61
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            25888
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             4768
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.972
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2320
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      2.178
_refine_ls_R_factor_all          0.2256
_refine_ls_R_factor_gt           0.1216
_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)+(0.0650P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2600
_refine_ls_wR_factor_ref         0.2872
_reflns_number_gt                975
_reflns_number_total             2320
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg201052k_si_002.cif
_cod_data_source_block           dip123
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'F d d d'
_cod_database_code               4501310
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/4, -y+1/4, z'
'x, -y+1/4, -z+1/4'
'-x+1/4, y, -z+1/4'
'x, y+1/2, z+1/2'
'-x+1/4, -y+3/4, z+1/2'
'x, -y+3/4, -z+3/4'
'-x+1/4, y+1/2, -z+3/4'
'x+1/2, y, z+1/2'
'-x+3/4, -y+1/4, z+1/2'
'x+1/2, -y+1/4, -z+3/4'
'-x+3/4, y, -z+3/4'
'x+1/2, y+1/2, z'
'-x+3/4, -y+3/4, z'
'x+1/2, -y+3/4, -z+1/4'
'-x+3/4, y+1/2, -z+1/4'
'-x, -y, -z'
'x-1/4, y-1/4, -z'
'-x, y-1/4, z-1/4'
'x-1/4, -y, z-1/4'
'-x, -y+1/2, -z+1/2'
'x-1/4, y+1/4, -z+1/2'
'-x, y+1/4, z+1/4'
'x-1/4, -y+1/2, z+1/4'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-1/4, -z+1/2'
'-x+1/2, y-1/4, z+1/4'
'x+1/4, -y, z+1/4'
'-x+1/2, -y+1/2, -z'
'x+1/4, y+1/4, -z'
'-x+1/2, y+1/4, z-1/4'
'x+1/4, -y+1/2, z-1/4'
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
C1 C 0.0743(2) 0.2738(9) 0.2931(3) 0.095(2) Uani 1 1 d .
C2 C 0.0795(2) 0.4309(10) 0.2119(4) 0.125(3) Uani 1 1 d .
H2 H 0.0720 0.4905 0.1840 0.150 Uiso 1 1 calc R
C3 C 0.1050(2) 0.4108(10) 0.2138(3) 0.131(3) Uani 1 1 d .
H3 H 0.1154 0.4562 0.1870 0.157 Uiso 1 1 calc R
C4 C 0.11626(16) 0.3202(9) 0.2567(4) 0.110(3) Uani 1 1 d .
H4 H 0.1341 0.3091 0.2583 0.132 Uiso 1 1 calc R
C5 C 0.10090(19) 0.2471(8) 0.2967(3) 0.093(2) Uani 1 1 d .
C6 C 0.11091(14) 0.1493(8) 0.3388(3) 0.094(2) Uani 1 1 d .
C7 C 0.09441(19) 0.0940(9) 0.3766(3) 0.104(2) Uani 1 1 d .
H7 H 0.1007 0.0339 0.4058 0.124 Uiso 1 1 calc R
C8 C 0.0677(2) 0.1251(9) 0.3732(3) 0.112(3) Uani 1 1 d .
H8 H 0.0572 0.0896 0.4014 0.134 Uiso 1 1 calc R
C9 C 0.0565(2) 0.2052(9) 0.3303(3) 0.101(2) Uani 1 1 d .
C10 C 0.0116(2) 0.1194(15) 0.3520(4) 0.185(5) Uani 1 1 d .
H10A H 0.0177 0.0076 0.3514 0.222 Uiso 1 1 calc R
H10B H 0.0107 0.1533 0.3897 0.222 Uiso 1 1 calc R
C11 C -0.0129(3) 0.1233(18) 0.3304(5) 0.195(5) Uani 1 1 d .
H11A H -0.0195 0.2338 0.3330 0.234 Uiso 1 1 calc R
H11B H -0.0240 0.0540 0.3521 0.234 Uiso 1 1 calc R
Cl1 Cl 0.05194(8) 0.3858(4) 0.03244(13) 0.1610(15) Uani 1 1 d D
H1N H 0.0475(4) 0.389(8) 0.248(3) 0.10(2) Uiso 1 1 d D
N1 N 0.06496(15) 0.3655(8) 0.2501(3) 0.114(2) Uani 1 1 d D
N2 N 0.03105(17) 0.2247(8) 0.3234(2) 0.126(2) Uani 1 1 d .
H2N H 0.0257 0.2999 0.3018 0.152 Uiso 1 1 calc R
O1 O -0.01434(12) 0.0727(8) 0.2761(2) 0.141(2) Uani 1 1 d D
H1 H 0.0002 0.0510 0.2650 0.211 Uiso 1 1 calc RD
O2 O 0.06898(15) 0.4018(11) -0.0091(3) 0.195(3) Uani 1 1 d .
O3 O 0.0437(2) 0.2350(10) 0.0434(3) 0.226(4) Uani 1 1 d .
O4 O 0.0549(3) 0.4848(11) 0.0750(4) 0.276(7) Uani 1 1 d D
O5 O 0.0272(3) 0.455(2) 0.0047(10) 0.276(12) Uani 0.50 1 d PD
O5' O 0.0781(2) 0.386(4) 0.0652(7) 0.334(19) Uani 0.50 1 d PD
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'
Cl Cl 0.1484 0.1585 '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_3
N1 C1 C5 118.5(7) .
N1 C1 C9 118.7(9) .
C5 C1 C9 122.7(8) .
N1 C2 C3 119.4(8) .
N1 C2 H2 120.3 .
C3 C2 H2 120.3 .
C2 C3 C4 119.9(8) .
C2 C3 H3 120.0 .
C4 C3 H3 120.0 .
C5 C4 C3 120.9(8) .
C5 C4 H4 119.5 .
C3 C4 H4 119.5 .
C1 C5 C4 116.7(8) .
C1 C5 C6 119.9(7) .
C4 C5 C6 123.4(9) .
C7 C6 C5 117.9(8) .
C7 C6 C6 121.7(7) 2
C5 C6 C6 120.3(6) 2
C6 C7 C8 121.5(7) .
C6 C7 H7 119.3 .
C8 C7 H7 119.3 .
C9 C8 C7 123.2(8) .
C9 C8 H8 118.4 .
C7 C8 H8 118.4 .
N2 C9 C8 124.9(8) .
N2 C9 C1 120.8(8) .
C8 C9 C1 114.3(9) .
C11 C10 N2 115.1(9) .
C11 C10 H10A 108.5 .
N2 C10 H10A 108.5 .
C11 C10 H10B 108.5 .
N2 C10 H10B 108.5 .
H10A C10 H10B 107.5 .
C10 C11 O1 114.2(10) .
C10 C11 H11A 108.7 .
O1 C11 H11A 108.7 .
C10 C11 H11B 108.7 .
O1 C11 H11B 108.7 .
H11A C11 H11B 107.6 .
O4 Cl1 O3 116.2(5) .
O4 Cl1 O2 117.3(6) .
O3 Cl1 O2 116.7(6) .
O4 Cl1 O5 102.5(10) .
O3 Cl1 O5 99.2(9) .
O2 Cl1 O5 99.8(10) .
O4 Cl1 O5' 59.9(10) .
O3 Cl1 O5' 100.1(12) .
O2 Cl1 O5' 80.0(7) .
O5 Cl1 O5' 158.4(15) .
C2 N1 C1 124.5(8) .
C2 N1 H1N 116(4) .
C1 N1 H1N 120(4) .
C9 N2 C10 122.2(7) .
C9 N2 H2N 118.9 .
C10 N2 H2N 118.9 .
C11 O1 H1 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.387(9) .
C1 C5 1.398(9) .
C1 C9 1.417(10) .
C2 N1 1.317(10) .
C2 C3 1.335(10) .
C2 H2 0.9300 .
C3 C4 1.417(11) .
C3 H3 0.9300 .
C4 C5 1.401(10) .
C4 H4 0.9300 .
C5 C6 1.409(9) .
C6 C7 1.343(9) .
C6 C6 1.515(14) 2
C7 C8 1.411(10) .
C7 H7 0.9300 .
C8 C9 1.371(10) .
C8 H8 0.9300 .
C9 N2 1.341(9) .
C10 C11 1.378(13) .
C10 N2 1.504(12) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 O1 1.401(13) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
Cl1 O4 1.334(7) .
Cl1 O3 1.336(7) .
Cl1 O2 1.358(6) .
Cl1 O5 1.559(16) .
Cl1 O5' 1.578(11) .
N1 H1N 0.928(16) .
N2 H2N 0.8600 .
O1 H1 0.8200 .
