#------------------------------------------------------------------------------
#$Date: 2022-08-30 02:16:27 +0300 (Tue, 30 Aug 2022) $
#$Revision: 277448 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/10/7711086.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_7711086
loop_
_publ_author_name
'Peppas, Anastassios'
'Sokalis, Demetrios'
'Perganti, Dorothea'
'Schnakenburg, Gregor'
'Falaras, Polycarpos'
'Philippopoulos, athanassios'
_publ_section_title
;
 Sterically demanding pyridine-quinoline anchoring ligands as building
 blocks for copper(I)-based dye-sensitized solar cells (DSSCs) complexes
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT02382B
_journal_year                    2022
_chemical_formula_moiety         'C16 H12 N2 O2'
_chemical_formula_sum            'C16 H12 N2 O2'
_chemical_formula_weight         264.28
_chemical_name_systematic        TP16H
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-09-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.21 svn.r3230 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2022-07-07 deposited with the CCDC.	2022-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9065(3)
_cell_length_b                   13.8542(8)
_cell_length_c                   18.1645(11)
_cell_measurement_reflns_used    7309
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.38
_cell_measurement_theta_min      4.01
_cell_volume                     1234.74(13)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.02
_diffrn_detector                 'Bruker Photon100 detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       'fine slicing ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0989
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18142
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.747
_diffrn_reflns_theta_min         4.013
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3703
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1747 before and 0.0938 after correction.
The Ratio of minimum to maximum transmission is 0.4914.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0542P)²+0.1325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.673
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1943
_reflns_number_total             2230
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt02382b1.cif
_cod_data_source_block           6p-Mepqca
_cod_database_code               7711086
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.899
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8(5) 0.2(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6876(5) 0.69003(14) 0.65946(11) 0.0270(5) Uani 1 1 d . . . . .
O2 O 0.8905(5) 0.75518(14) 0.56077(11) 0.0245(5) Uani 1 1 d . . . . .
H2 H 0.8734 0.8063 0.5852 0.037 Uiso 1 1 calc GR . . . .
N1 N 0.8723(5) 0.41677(16) 0.47655(12) 0.0158(5) Uani 1 1 d . . . . .
N2 N 1.3706(5) 0.56295(16) 0.38126(12) 0.0156(5) Uani 1 1 d . . . . .
C1 C 0.6848(6) 0.4221(2) 0.53173(15) 0.0157(6) Uani 1 1 d . . . . .
C2 C 0.6343(6) 0.5077(2) 0.57363(15) 0.0164(6) Uani 1 1 d . . . . .
C3 C 0.7973(6) 0.58914(19) 0.55526(15) 0.0166(6) Uani 1 1 d . . . . .
C4 C 0.9822(6) 0.5830(2) 0.49975(16) 0.0170(6) Uani 1 1 d . . . . .
H4 H 1.0890 0.6377 0.4871 0.020 Uiso 1 1 calc R . . . .
C5 C 1.0164(6) 0.4953(2) 0.46061(16) 0.0152(6) Uani 1 1 d . . . . .
C6 C 0.5343(6) 0.3370(2) 0.54734(16) 0.0187(6) Uani 1 1 d . . . . .
H6 H 0.5695 0.2799 0.5200 0.022 Uiso 1 1 calc R . . . .
C7 C 0.3402(6) 0.3361(2) 0.60093(16) 0.0206(6) Uani 1 1 d . . . . .
H7 H 0.2419 0.2785 0.6110 0.025 Uiso 1 1 calc R . . . .
C8 C 0.2850(6) 0.4209(2) 0.64155(16) 0.0227(7) Uani 1 1 d . . . . .
H8 H 0.1483 0.4201 0.6786 0.027 Uiso 1 1 calc R . . . .
C9 C 0.4267(6) 0.5044(2) 0.62807(15) 0.0194(6) Uani 1 1 d . . . . .
H9 H 0.3854 0.5608 0.6556 0.023 Uiso 1 1 calc R . . . .
C10 C 0.7816(6) 0.6826(2) 0.59777(16) 0.0188(6) Uani 1 1 d . . . . .
C11 C 1.2195(6) 0.4850(2) 0.39999(16) 0.0156(6) Uani 1 1 d . . . . .
C12 C 1.2491(6) 0.3968(2) 0.36409(16) 0.0208(7) Uani 1 1 d . . . . .
H12 H 1.1387 0.3432 0.3774 0.025 Uiso 1 1 calc R . . . .
C13 C 1.4399(7) 0.3883(2) 0.30922(16) 0.0213(7) Uani 1 1 d . . . . .
H13 H 1.4628 0.3285 0.2844 0.026 Uiso 1 1 calc R . . . .
C14 C 1.5980(7) 0.4664(2) 0.29011(15) 0.0198(7) Uani 1 1 d . . . . .
H14 H 1.7317 0.4612 0.2525 0.024 Uiso 1 1 calc R . . . .
C15 C 1.5576(6) 0.5537(2) 0.32730(15) 0.0172(6) Uani 1 1 d . . . . .
C16 C 1.7198(7) 0.6414(2) 0.30753(18) 0.0258(7) Uani 1 1 d . . . . .
H16A H 1.5958 0.6945 0.2954 0.039 Uiso 1 1 calc GR . . . .
H16B H 1.8354 0.6270 0.2649 0.039 Uiso 1 1 calc GR . . . .
H16C H 1.8345 0.6600 0.3493 0.039 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C10 O2 H2 109.5 . . ?
C5 N1 C1 118.4(2) . . ?
C15 N2 C11 118.7(2) . . ?
N1 C1 C2 123.6(3) . . ?
N1 C1 C6 117.0(2) . . ?
C6 C1 C2 119.5(3) . . ?
C3 C2 C1 115.8(3) . . ?
C9 C2 C1 117.8(3) . . ?
C9 C2 C3 126.3(3) . . ?
C2 C3 C10 122.1(3) . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 C10 117.9(3) . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(3) . . ?
C5 C4 H4 119.8 . . ?
N1 C5 C4 121.9(3) . . ?
N1 C5 C11 116.0(2) . . ?
C4 C5 C11 122.1(3) . . ?
C1 C6 H6 119.5 . . ?
C7 C6 C1 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.0(3) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C2 C9 H9 119.5 . . ?
C8 C9 C2 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
O1 C10 O2 123.9(3) . . ?
O1 C10 C3 124.3(3) . . ?
O2 C10 C3 111.8(2) . . ?
N2 C11 C5 118.4(2) . . ?
N2 C11 C12 121.7(3) . . ?
C12 C11 C5 119.9(3) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.5(3) . . ?
C15 C14 H14 120.7 . . ?
N2 C15 C14 122.0(3) . . ?
N2 C15 C16 117.4(2) . . ?
C14 C15 C16 120.7(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
O1 C10 1.216(4) . ?
O2 H2 0.8400 . ?
O2 C10 1.322(4) . ?
N1 C1 1.362(4) . ?
N1 C5 1.329(4) . ?
N2 C11 1.353(4) . ?
N2 C15 1.349(4) . ?
C1 C2 1.431(4) . ?
C1 C6 1.419(4) . ?
C2 C3 1.422(4) . ?
C2 C9 1.420(4) . ?
C3 C4 1.359(4) . ?
C3 C10 1.510(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.418(4) . ?
C5 C11 1.492(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.362(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.413(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.371(4) . ?
C9 H9 0.9500 . ?
C11 C12 1.393(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.373(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.375(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.400(4) . ?
C15 C16 1.496(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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 -1.1(4) . . . . ?
N1 C1 C2 C9 178.0(3) . . . . ?
N1 C1 C6 C7 -179.1(3) . . . . ?
N1 C5 C11 N2 179.6(3) . . . . ?
N1 C5 C11 C12 -0.2(4) . . . . ?
N2 C11 C12 C13 1.2(4) . . . . ?
C1 N1 C5 C4 0.7(4) . . . . ?
C1 N1 C5 C11 179.7(2) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C1 C2 C3 C10 -175.8(2) . . . . ?
C1 C2 C9 C8 1.9(4) . . . . ?
C1 C6 C7 C8 0.4(4) . . . . ?
C2 C1 C6 C7 0.9(4) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C2 C3 C10 O1 19.1(4) . . . . ?
C2 C3 C10 O2 -163.0(3) . . . . ?
C3 C2 C9 C8 -179.1(3) . . . . ?
C3 C4 C5 N1 -0.3(4) . . . . ?
C3 C4 C5 C11 -179.2(3) . . . . ?
C4 C3 C10 O1 -158.3(3) . . . . ?
C4 C3 C10 O2 19.7(4) . . . . ?
C4 C5 C11 N2 -1.4(4) . . . . ?
C4 C5 C11 C12 178.8(3) . . . . ?
C5 N1 C1 C2 0.0(4) . . . . ?
C5 N1 C1 C6 180.0(3) . . . . ?
C5 C11 C12 C13 -179.0(3) . . . . ?
C6 C1 C2 C3 178.9(3) . . . . ?
C6 C1 C2 C9 -2.0(4) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
C7 C8 C9 C2 -0.7(4) . . . . ?
C9 C2 C3 C4 -177.5(3) . . . . ?
C9 C2 C3 C10 5.2(4) . . . . ?
C10 C3 C4 C5 176.5(2) . . . . ?
C11 N2 C15 C14 0.4(4) . . . . ?
C11 N2 C15 C16 179.6(3) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C14 C15 N2 0.5(4) . . . . ?
C13 C14 C15 C16 -178.7(3) . . . . ?
C15 N2 C11 C5 178.9(2) . . . . ?
C15 N2 C11 C12 -1.2(4) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8(5)
2 0.2(5)
