#------------------------------------------------------------------------------
#$Date: 2017-01-09 04:09:14 +0100 (lun 09 de ene de 2017) $
#$Revision: 190088 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/69/7226926.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_7226926
loop_
_publ_author_name
'Perera, M. D.'
'Desper, J.'
'Sinha, A. S.'
'Aakeröy, C. B.'
_publ_section_title
;
 Impact and importance of electrostatic potential calculations for
 predicting structural patterns of hydrogen and halogen bonding
;
_journal_issue                   44
_journal_name_full               CrystEngComm
_journal_page_first              8631
_journal_paper_doi               10.1039/C6CE02089E
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety
;
(C10 H7 N3)2 (C6 H10 O4)
;
_chemical_formula_sum            'C26 H24 N6 O4'
_chemical_formula_weight         484.51
_chemical_name_systematic
;
Mp-p1b-H11 {[1,2,3]Triazolo[1,5-a]quinoline}2, HOOC-(CH2)4-COOH
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-09-27 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.111(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.9843(6)
_cell_length_b                   25.501(2)
_cell_length_c                   6.8129(6)
_cell_measurement_reflns_used    5232
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.84
_cell_measurement_theta_min      3.07
_cell_volume                     1153.30(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11766
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         32.05
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_correction_T_min  0.9584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0477
_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)+(0.0600P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                2796
_reflns_number_total             3681
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce02089e2.cif
_cod_data_source_block           A1HB6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7226924--7226932.cif.
;
_cod_original_cell_volume        1153.32(17)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7226926
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N11 N 0.50408(13) 0.32391(4) 0.48722(14) 0.0184(2) Uani 1 1 d .
N12 N 0.31017(14) 0.33950(4) 0.42642(16) 0.0243(2) Uani 1 1 d .
N13 N 0.31603(15) 0.39131(4) 0.42717(17) 0.0264(2) Uani 1 1 d .
C14 C 0.50754(18) 0.40843(5) 0.48602(18) 0.0239(2) Uani 1 1 d .
H14 H 0.5488 0.4441 0.4985 0.029 Uiso 1 1 calc R
C15 C 0.63460(17) 0.36541(4) 0.52544(17) 0.0192(2) Uani 1 1 d .
C16 C 0.84501(17) 0.35576(5) 0.58296(18) 0.0231(2) Uani 1 1 d .
H16 H 0.9383 0.3840 0.6112 0.028 Uiso 1 1 calc R
C17 C 0.90974(17) 0.30574(5) 0.59663(18) 0.0239(2) Uani 1 1 d .
H17 H 1.0501 0.2990 0.6312 0.029 Uiso 1 1 calc R
C18 C 0.77226(17) 0.26224(5) 0.56039(16) 0.0212(2) Uani 1 1 d .
C19 C 0.8347(2) 0.20965(5) 0.57751(19) 0.0283(3) Uani 1 1 d .
H19 H 0.9744 0.2018 0.6149 0.034 Uiso 1 1 calc R
C20 C 0.6979(2) 0.16931(5) 0.54126(19) 0.0309(3) Uani 1 1 d .
H20 H 0.7434 0.1340 0.5525 0.037 Uiso 1 1 calc R
C21 C 0.4920(2) 0.18010(5) 0.48791(19) 0.0293(3) Uani 1 1 d .
H21 H 0.3981 0.1520 0.4635 0.035 Uiso 1 1 calc R
C22 C 0.42410(18) 0.23106(5) 0.47040(18) 0.0238(2) Uani 1 1 d .
H22 H 0.2842 0.2385 0.4351 0.029 Uiso 1 1 calc R
C23 C 0.56428(17) 0.27150(4) 0.50544(16) 0.0192(2) Uani 1 1 d .
C31 C -0.02700(17) 0.49104(5) 0.24785(17) 0.0216(2) Uani 1 1 d .
O31 O -0.03922(13) 0.43939(4) 0.24246(14) 0.0294(2) Uani 1 1 d .
H31 H 0.089(2) 0.4255(6) 0.311(2) 0.035 Uiso 1 1 d .
O32 O 0.12995(13) 0.51442(3) 0.32405(15) 0.0317(2) Uani 1 1 d .
C32 C -0.22513(17) 0.51842(4) 0.15471(19) 0.0233(2) Uani 1 1 d .
H32A H -0.2064 0.5456 0.0585 0.028 Uiso 1 1 calc R
H32B H -0.2605 0.5367 0.2669 0.028 Uiso 1 1 calc R
C33 C -0.40309(16) 0.48428(4) 0.03869(18) 0.0221(2) Uani 1 1 d .
H33A H -0.3741 0.4676 -0.0802 0.026 Uiso 1 1 calc R
H33B H -0.4210 0.4561 0.1313 0.026 Uiso 1 1 calc R
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
N12 N11 C15 112.14(9) .
N12 N11 C23 123.81(9) .
C15 N11 C23 124.04(9) .
N13 N12 N11 105.48(9) .
N12 N13 C14 110.64(10) .
N13 C14 C15 108.61(10) .
N13 C14 H14 125.7 .
C15 C14 H14 125.7 .
N11 C15 C14 103.13(10) .
N11 C15 C16 119.32(10) .
C14 C15 C16 137.51(11) .
C17 C16 C15 118.67(11) .
C17 C16 H16 120.7 .
C15 C16 H16 120.7 .
C16 C17 C18 121.81(11) .
C16 C17 H17 119.1 .
C18 C17 H17 119.1 .
C23 C18 C19 116.87(11) .
C23 C18 C17 119.81(10) .
C19 C18 C17 123.33(11) .
C20 C19 C18 121.34(12) .
C20 C19 H19 119.3 .
C18 C19 H19 119.3 .
C19 C20 C21 120.12(12) .
C19 C20 H20 119.9 .
C21 C20 H20 119.9 .
C22 C21 C20 120.53(12) .
C22 C21 H21 119.7 .
C20 C21 H21 119.7 .
C21 C22 C23 118.70(12) .
C21 C22 H22 120.7 .
C23 C22 H22 120.7 .
C22 C23 N11 121.24(10) .
C22 C23 C18 122.44(11) .
N11 C23 C18 116.32(10) .
O32 C31 O31 122.97(11) .
O32 C31 C32 122.88(11) .
O31 C31 C32 114.13(10) .
C31 O31 H31 108.7(9) .
C31 C32 C33 116.71(10) .
C31 C32 H32A 108.1 .
C33 C32 H32A 108.1 .
C31 C32 H32B 108.1 .
C33 C32 H32B 108.1 .
H32A C32 H32B 107.3 .
C33 C33 C32 111.96(12) 3_465
C33 C33 H33A 109.2 3_465
C32 C33 H33A 109.2 .
C33 C33 H33B 109.2 3_465
C32 C33 H33B 109.2 .
H33A C33 H33B 107.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 N12 1.3473(13) .
N11 C15 1.3680(14) .
N11 C23 1.3951(14) .
N12 N13 1.3217(14) .
N13 C14 1.3443(16) .
C14 C15 1.3837(16) .
C14 H14 0.9500 .
C15 C16 1.4198(16) .
C16 C17 1.3467(17) .
C16 H16 0.9500 .
C17 C18 1.4373(17) .
C17 H17 0.9500 .
C18 C23 1.4028(16) .
C18 C19 1.4039(16) .
C19 C20 1.3730(19) .
C19 H19 0.9500 .
C20 C21 1.397(2) .
C20 H20 0.9500 .
C21 C22 1.3758(17) .
C21 H21 0.9500 .
C22 C23 1.3905(16) .
C22 H22 0.9500 .
C31 O32 1.2136(14) .
C31 O31 1.3198(15) .
C31 C32 1.5031(15) .
O31 H31 0.940(16) .
C32 C33 1.5222(15) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C33 1.520(2) 3_465
C33 H33A 0.9900 .
C33 H33B 0.9900 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O31 H31 N13 0.940(16) 1.767(16) 2.7022(13) 172.5(14)
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_4
C15 N11 N12 N13 -0.50(13) .
C23 N11 N12 N13 -179.45(10) .
N11 N12 N13 C14 0.16(13) .
N12 N13 C14 C15 0.22(14) .
N12 N11 C15 C14 0.61(13) .
C23 N11 C15 C14 179.56(10) .
N12 N11 C15 C16 -177.45(10) .
C23 N11 C15 C16 1.50(16) .
N13 C14 C15 N11 -0.49(13) .
N13 C14 C15 C16 177.01(13) .
N11 C15 C16 C17 0.49(17) .
C14 C15 C16 C17 -176.72(13) .
C15 C16 C17 C18 -1.78(17) .
C16 C17 C18 C23 1.19(17) .
C16 C17 C18 C19 -178.62(11) .
C23 C18 C19 C20 0.23(17) .
C17 C18 C19 C20 -179.95(11) .
C18 C19 C20 C21 -0.58(18) .
C19 C20 C21 C22 0.23(19) .
C20 C21 C22 C23 0.44(18) .
C21 C22 C23 N11 179.14(10) .
C21 C22 C23 C18 -0.81(17) .
N12 N11 C23 C22 -3.16(17) .
C15 N11 C23 C22 178.01(10) .
N12 N11 C23 C18 176.78(10) .
C15 N11 C23 C18 -2.04(16) .
C19 C18 C23 C22 0.47(17) .
C17 C18 C23 C22 -179.36(11) .
C19 C18 C23 N11 -179.47(10) .
C17 C18 C23 N11 0.70(15) .
O32 C31 C32 C33 171.70(12) .
O31 C31 C32 C33 -9.34(15) .
C31 C32 C33 C33 177.01(12) 3_465
