#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:52:17 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228956 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/97/7229767.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_7229767
loop_
_publ_author_name
'Fedyanin, Ivan V.'
'Karnoukhova, Valentina A.'
'Lyssenko, Konstantin A.'
_publ_section_title
;
 Conformational analysis of a supramolecular synthon: a case study of
 8-hydroxyquinoline
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              652
_journal_paper_doi               10.1039/C7CE01928A
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C9 H7 N O'
_chemical_formula_sum            'C9 H7 N O'
_chemical_formula_weight         145.16
_chemical_name_common            quinoline-8-ol
_chemical_name_systematic        8-hydroxyquinoline
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             '06-Jun-06 T15:16:19-00:00'
_audit_creation_method           'Modified XDCIF output'
_audit_update_record
;
2017-11-06 deposited with the CCDC.
2017-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   24.9340(4)
_cell_length_b                   28.5658(4)
_cell_length_c                   3.77780(10)
_cell_measurement_reflns_used    6533
_cell_measurement_temperature    100
_cell_measurement_theta_max      60.65
_cell_measurement_theta_min      2.17
_cell_volume                     2690.77(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'
_computing_structure_refinement  'Volkov et al, (2006)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX II CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker APEX II'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_limit_h_max       60
_diffrn_reflns_limit_h_min       -60
_diffrn_reflns_limit_k_max       69
_diffrn_reflns_limit_k_min       -67
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            75800
_diffrn_reflns_theta_full        59.997
_diffrn_reflns_theta_max         59.997
_diffrn_reflns_theta_min         2.168
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.096
_refine_diff_density_rms         0.022
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.285
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1
_refine_ls_number_reflns         4966
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.02
_refine_ls_R_factor_gt           0.014
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
        calc w1 = [Fo*sqrt(w2) + sqrt(Fo²w2² + sqrt(w2²))]²
        where
     calc w2 = q/[s²(Fo²) + (0.01 P)² + 0.01 P + 0.00 + 0.00 sin(th)]
     where P = (0.3333 Fo² + 0.6667 Fc²)
           q = 1.0
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.012
_reflns_number_gt                4966
_reflns_number_total             5843
_reflns_threshold_expression     F>3σ(F)
_cod_data_source_file            c7ce01928a2.cif
_cod_data_source_block           hq-mm
_cod_depositor_comments
'Adding full bibliography for 7229766--7229767.cif.'
_cod_database_code               7229767
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +x,+y,+z
2 -x,-y,+z
3 1/4+x,1/4-y,1/4+z
4 1/4-x,1/4+y,1/4+z
5 1/2+x,1/2+y,+z
6 1/2-x,1/2-y,+z
7 3/4+x,3/4-y,1/4+z
8 3/4-x,3/4+y,1/4+z
9 1/2+x,+y,1/2+z
10 1/2-x,-y,1/2+z
11 3/4+x,1/4-y,3/4+z
12 3/4-x,1/4+y,3/4+z
13 +x,1/2+y,1/2+z
14 -x,1/2-y,1/2+z
15 1/4+x,3/4-y,3/4+z
16 1/4-x,3/4+y,3/4+z
loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(1) C(8) Z O(1) H(1) X
N(1) C(4) Z N(1) C(2) X
C(2) C(3) Z C(2) N(1) X
C(3) C(4) Z C(3) C(2) X
C(4) C(4A) Z C(4) C(3) X
C(4A) C(8A) Z C(4A) C(4) X
C(5) C(6) Z C(5) C(4A) X
C(6) C(7) Z C(6) C(5) X
C(7) C(8) Z C(7) C(6) X
C(8) O(1) Z C(8) C(7) X
C(8A) N(1) Z C(8A) C(4A) X
H(1) O(1) Z H(1) C(8) X
H(2) C(2) Z H(2) N(1) X
H(3) C(3) Z H(3) C(4) X
H(4) C(4) Z H(4) C(3) X
H(5) C(5) Z H(5) C(6) X
H(6) C(6) Z H(6) C(5) X
H(7) C(7) Z H(7) C(8) X
loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
O(1) 6.1034(15) 0 -0.084(6) 0.015(9) -0.025(4) -0.037(4) 0.029(3) -0.016(4)
0.004(4) -0.044(4) 0.046(6) -0.020(5) -0.002(7) -0.061(9) -0.003(7) -0.013(9)
0.001(5) 0 0 0 0 0 0 0 0 0 1.003123 0.985(15) 0.985(15) 0.985(15) 0.985(15)
0.985(15)
N(1) 5.20(2) 0 0.007(6) -0.012(10) -0.111(5) 0.126(4) 0.013(4) -0.012(4)
0.114(4) -0.012(4) -0.088(6) -0.005(6) -0.008(7) 0.087(8) 0.010(8) -0.026(9)
-0.004(6) 0 0 0 0 0 0 0 0 0 1.001262 0.984(9) 0.984(9) 0.984(9) 0.984(9)
0.984(9)
C(2) 3.98(2) 0 0.041(8) 0.020(14) -0.009(7) 0.115(6) -0.005(5) 0.012(6)
0.176(6) -0.017(6) 0.240(9) -0.016(8) 0.013(10) -0.221(11) 0.017(11) 0.021(11)
0.013(9) 0 0 0 0 0 0 0 0 0 1.019097 0.974(7) 0.974(7) 0.974(7) 0.974(7)
0.974(7)
C(3) 4.06(2) 0 0.029(8) 0.023(13) 0.041(7) 0.124(6) 0.004(5) -0.002(6) 0.155(6)
-0.027(6) 0.211(10) -0.011(8) 0.002(12) -0.193(9) 0.006(9) 0.017(11) 0.001(8) 0
0 0 0 0 0 0 0 0 1.018636 0.989(8) 0.989(8) 0.989(8) 0.989(8) 0.989(8)
C(4) 4.02(2) 0 0.023(7) 0.030(13) -0.002(8) 0.099(6) -0.014(5) -0.017(6)
0.179(5) -0.007(6) 0.223(10) -0.000(8) 0.000(7) -0.123(11) 0.011(9) -0.021(8)
0.013(12) 0 0 0 0 0 0 0 0 0 1.015322 0.998(9) 0.998(9) 0.998(9) 0.998(9)
0.998(9)
C(4A) 4.09(2) 0 -0.005(8) 0.014(13) -0.025(7) 0.090(6) 0.004(5) -0.015(6)
0.187(6) 0.015(6) 0.233(9) -0.020(8) 0.014(9) -0.162(10) 0.007(11) -0.016(11)
0.009(8) 0 0 0 0 0 0 0 0 0 1.016075 0.981(8) 0.981(8) 0.981(8) 0.981(8)
0.981(8)
C(5) 4.05(2) 0 0.011(7) 0.024(14) 0.047(9) 0.125(6) 0.007(6) -0.025(6) 0.131(5)
0.010(6) 0.246(11) -0.018(8) 0.005(8) -0.155(11) 0.001(8) -0.020(8) 0.013(12) 0
0 0 0 0 0 0 0 0 1.017058 0.978(9) 0.978(9) 0.978(9) 0.978(9) 0.978(9)
C(6) 3.98(2) 0 0.025(9) 0.023(13) 0.040(7) 0.106(6) -0.046(6) 0.006(6) 0.176(6)
0.007(6) 0.238(8) 0.006(8) 0.035(10) -0.135(10) -0.002(10) -0.066(12) 0.014(8)
0 0 0 0 0 0 0 0 0 1.014679 0.980(8) 0.980(8) 0.980(8) 0.980(8) 0.980(8)
C(7) 4.03(2) 0 0.000(9) 0.026(13) 0.024(8) 0.077(5) -0.016(6) 0.000(6) 0.133(6)
0.005(6) 0.196(10) -0.005(8) 0.016(11) -0.165(9) 0.008(9) -0.056(11) 0.010(7) 0
0 0 0 0 0 0 0 0 1.018042 0.992(10) 0.992(10) 0.992(10) 0.992(10) 0.992(10)
C(8) 4.11(2) 0 0.033(8) -0.015(12) -0.049(7) 0.078(6) -0.029(5) 0.022(6)
0.209(6) 0.017(6) 0.324(8) -0.012(9) -0.016(10) -0.146(9) -0.002(10) 0.015(12)
-0.005(8) 0 0 0 0 0 0 0 0 0 1.010683 0.978(7) 0.978(7) 0.978(7) 0.978(7)
0.978(7)
C(8A) 4.14(2) 0 0.030(8) 0.003(14) -0.011(7) 0.089(5) -0.003(5) 0.005(6)
0.158(6) 0.026(6) 0.268(10) 0.045(8) 0.006(12) -0.183(9) -0.001(9) -0.049(13)
0.017(8) 0 0 0 0 0 0 0 0 0 1.01127 0.971(7) 0.971(7) 0.971(7) 0.971(7) 0.971(7)
H(1) 0.775(8) 0 0 0 0.270(7) 0.223(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.2 1.2 1.2 1.2 1.2 1.2
H(2) 0.909(8) 0 0 0 0.145(6) 0.107(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.2 1.2 1.2 1.2 1.2 1.2
H(3) 0.889(8) 0 0 0 0.151(7) 0.081(10) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.2 1.2 1.2 1.2 1.2 1.2
H(4) 0.907(8) 0 0 0 0.153(7) 0.101(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.2 1.2 1.2 1.2 1.2 1.2
H(5) 0.939(8) 0 0 0 0.144(7) 0.106(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.2 1.2 1.2 1.2 1.2 1.2
H(6) 0.927(8) 0 0 0 0.144(7) 0.107(10) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.2 1.2 1.2 1.2 1.2 1.2
H(7) 0.902(8) 0 0 0 0.155(7) 0.065(10) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.2 1.2 1.2 1.2 1.2 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_occupancy
_atom_site_symmetry_multiplicity
O(1) O 0.066547(5) -0.032501(4) 0.1504(8) 0.016 1 16
N(1) N 0.033157(5) 0.050333(4) 0.4586(8) 0.011 1 16
C(2) C 0.018267(6) 0.089633(5) 0.6151(8) 0.012 1 16
C(3) C 0.054070(6) 0.126280(5) 0.6993(8) 0.013 1 16
C(4) C 0.107466(6) 0.121281(5) 0.6174(8) 0.013 1 16
C(4A) C 0.125249(5) 0.079505(5) 0.4533(8) 0.011 1 16
C(5) C 0.179524(6) 0.071893(5) 0.3578(8) 0.013 1 16
C(6) C 0.193810(6) 0.030678(5) 0.1945(8) 0.013 1 16
C(7) C 0.155440(6) -0.004545(5) 0.1248(8) 0.013 1 16
C(8) C 0.102347(6) 0.001770(5) 0.2176(8) 0.011 1 16
C(8A) C 0.086144(5) 0.044625(4) 0.3806(8) 0.01 1 16
H(1) H 0.031049 -0.025606 0.254867 0.027 1 16
H(2) H -0.023629 0.093964 0.682172 0.029 1 16
H(3) H 0.039698 0.157848 0.826016 0.031 1 16
H(4) H 0.135649 0.148996 0.6767 0.031 1 16
H(5) H 0.209543 0.09829 0.411992 0.031 1 16
H(6) H 0.235125 0.025151 0.117546 0.031 1 16
H(7) H 0.167731 -0.0367 -0.003019 0.03 1 16
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(8) O(1) H(1) 111.87(6) 1_555 1_555 1_555 yes
C(2) N(1) C(8A) 118.059(12) 1_555 1_555 1_555 yes
N(1) C(2) C(3) 123.554(14) 1_555 1_555 1_555 yes
N(1) C(2) H(2) 118.22(6) 1_555 1_555 1_555 yes
C(3) C(2) H(2) 118.22(6) 1_555 1_555 1_555 yes
C(2) C(3) C(4) 118.995(13) 1_555 1_555 1_555 yes
C(2) C(3) H(3) 120.538(14) 1_555 1_555 1_555 yes
C(4) C(3) H(3) 120.467(14) 1_555 1_555 1_555 yes
C(3) C(4) C(4A) 119.307(13) 1_555 1_555 1_555 yes
C(3) C(4) H(4) 120.43(6) 1_555 1_555 1_555 yes
C(4A) C(4) H(4) 120.26(6) 1_555 1_555 1_555 yes
C(4) C(4A) C(5) 122.661(13) 1_555 1_555 1_555 yes
C(4) C(4A) C(8A) 117.431(12) 1_555 1_555 1_555 yes
C(5) C(4A) C(8A) 119.904(13) 1_555 1_555 1_555 yes
C(4A) C(5) C(6) 119.503(13) 1_555 1_555 1_555 yes
C(4A) C(5) H(5) 120.37(6) 1_555 1_555 1_555 yes
C(6) C(5) H(5) 120.13(7) 1_555 1_555 1_555 yes
C(5) C(6) C(7) 121.164(14) 1_555 1_555 1_555 yes
C(5) C(6) H(6) 119.46(6) 1_555 1_555 1_555 yes
C(7) C(6) H(6) 119.38(6) 1_555 1_555 1_555 yes
C(6) C(7) C(8) 120.566(13) 1_555 1_555 1_555 yes
C(6) C(7) H(7) 119.727(15) 1_555 1_555 1_555 yes
C(8) C(7) H(7) 119.708(15) 1_555 1_555 1_555 yes
O(1) C(8) C(7) 119.447(13) 1_555 1_555 1_555 yes
O(1) C(8) C(8A) 121.057(12) 1_555 1_555 1_555 yes
C(7) C(8) C(8A) 119.494(13) 1_555 1_555 1_555 yes
N(1) C(8A) C(4A) 122.638(12) 1_555 1_555 1_555 yes
N(1) C(8A) C(8) 118.014(12) 1_555 1_555 1_555 yes
C(4A) C(8A) C(8) 119.346(12) 1_555 1_555 1_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(8) 1.34897(18) 1_555 1_555 yes
O(1) H(1) 0.9890(12) 1_555 1_555 yes
N(1) C(2) 1.3220(2) 1_555 1_555 yes
N(1) C(8A) 1.36346(18) 1_555 1_555 yes
C(2) C(3) 1.4121(2) 1_555 1_555 yes
C(2) H(2) 1.0820(7) 1_555 1_555 yes
C(3) C(4) 1.3743(2) 1_555 1_555 yes
C(3) H(3) 1.0820(13) 1_555 1_555 yes
C(4) C(4A) 1.4161(2) 1_555 1_555 yes
C(4) H(4) 1.0820(6) 1_555 1_555 yes
C(4A) C(5) 1.4173(2) 1_555 1_555 yes
C(4A) C(8A) 1.42084(18) 1_555 1_555 yes
C(5) C(6) 1.3761(2) 1_555 1_555 yes
C(5) H(5) 1.0820(6) 1_555 1_555 yes
C(6) C(7) 1.4132(2) 1_555 1_555 yes
C(6) H(6) 1.0820(8) 1_555 1_555 yes
C(7) C(8) 1.3813(2) 1_555 1_555 yes
C(7) H(7) 1.0820(13) 1_555 1_555 yes
C(8) C(8A) 1.42868(19) 1_555 1_555 yes
