#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:04:51 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290134 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/08/1570808.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_1570808
loop_
_publ_author_name
'Lv, Youming'
'Ye, Hebo'
'You, Lei'
_publ_section_title
;
 Multiple control of azoquinoline based molecular photoswitches.
;
_journal_issue                   9
_journal_name_full               'Chemical science'
_journal_page_first              3290
_journal_page_last               3299
_journal_paper_doi               10.1039/d3sc05879d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C16 H11 N3 O2'
_chemical_formula_sum            'C16 H11 N3 O2'
_chemical_formula_weight         277.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-26
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-11-02 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.316(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9630(6)
_cell_length_b                   12.2129(10)
_cell_length_c                   15.0009(12)
_cell_measurement_reflns_used    7847
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      59.7020
_cell_measurement_theta_min      4.0150
_cell_volume                     1262.24(18)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00 -11.00   0.50    0.07    --  -78.14  89.00  66.00  134
  2  ω     -2.00  23.00   0.50    0.05    --   -1.41  89.00  66.00   50
  3  ω     59.00 108.00   0.50    0.07    --   75.32  77.00 150.00   98
  4  ω     81.00 129.00   0.50    0.07    --   75.32  89.00  66.00   96
  5  ω     94.00 148.00   0.50    0.07    --   75.32 125.00-120.00  108
  6  ω    -31.00  -4.00   0.50    0.07    --  -78.14  77.00-120.00   54
  7  ω    -87.00 -41.00   0.50    0.07    --  -78.14  77.00-120.00   92
  8  ω    -54.00  -1.00   0.50    0.07    --  -78.14  38.00 -90.00  106
  9  ω    -36.00  22.00   0.50    0.05    --   -1.41 -89.00 -49.00  116
 10  ω     -6.00  29.00   0.50    0.05    --   -1.41 -99.00  60.00   70
 11  ω     25.00 108.00   0.50    0.07    --   75.32-125.00 -30.00  166
 12  ω     67.00 111.00   0.50    0.07    --   75.32-125.00 -90.00   88
 13  ω     46.00  87.00   0.50    0.07    --   75.32-125.00-180.00   82
 14  ω     -8.00  31.00   0.50    0.05    --   -1.41 -99.00-180.00   78
 15  ω     25.00  89.00   0.50    0.07    --   75.32 -89.00 -49.00  128
 16  ω     21.00  60.00   0.50    0.07    --   75.32 -38.00 -60.00   78
 17  ω     21.00 110.00   0.50    0.07    --   75.32-125.00 120.00  178
 18  ω      2.00  70.00   0.50    0.07    --   75.32 -38.00   0.00  136
 19  ω    -11.00  22.00   0.50    0.05    --   -1.41 -57.00  90.00   66
 20  ω    -73.00 -30.00   0.50    0.05    --   -1.41 -57.00  90.00   86
 21  ω   -150.00 -56.00   0.50    0.07    --  -78.14 -57.00   0.00  188
 22  ω   -112.00 -81.00   0.50    0.07    --  -78.14 -89.00 -49.00   62
 23  ω   -149.00-124.00   0.50    0.07    --  -78.14-125.00  90.00   50
 24  ω   -121.00 -93.00   0.50    0.07    --  -78.14-125.00  90.00   56
 25  ω   -145.00 -96.00   0.50    0.07    --  -78.14 -99.00  60.00   98
 26  ω   -133.00-108.00   0.50    0.07    --  -78.14-125.00-150.00   50
 27  ω   -140.00 -95.00   0.50    0.07    --  -78.14 -99.00-180.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0797550000
_diffrn_orient_matrix_UB_12      0.0368223000
_diffrn_orient_matrix_UB_13      0.0809393000
_diffrn_orient_matrix_UB_21      0.1098266000
_diffrn_orient_matrix_UB_22      -0.0902844000
_diffrn_orient_matrix_UB_23      0.0121205000
_diffrn_orient_matrix_UB_31      0.1394092000
_diffrn_orient_matrix_UB_32      0.0500180000
_diffrn_orient_matrix_UB_33      -0.0378467000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14510
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.536
_diffrn_reflns_theta_min         4.075
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.519
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0589
_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)+(0.0869P)²+0.8999P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1703
_refine_ls_wR_factor_ref         0.1771
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2388
_reflns_number_total             2812
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05879d2.cif
_cod_data_source_block           E-2
_cod_depositor_comments
'Adding full bibliography for 1570804--1570808.cif.'
_cod_database_code               1570808
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L)
1.b Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.774
_oxdiff_exptl_absorpt_empirical_full_min 0.420
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O001 O 0.1806(2) 0.46005(11) 0.32530(9) 0.0340(4) Uani 1 1 d . . . . .
H001 H 0.205593 0.462492 0.381747 0.051 Uiso 1 1 calc R U . . .
O002 O 0.0970(2) 0.57317(12) 0.21301(9) 0.0379(4) Uani 1 1 d . . . . .
N003 N 0.2823(2) 0.32513(13) 0.47787(10) 0.0282(4) Uani 1 1 d . . . . .
N004 N 0.2648(2) 0.54041(13) 0.57245(10) 0.0286(4) Uani 1 1 d . . . . .
N005 N 0.2337(2) 0.54356(13) 0.48777(10) 0.0282(4) Uani 1 1 d . . . . .
C006 C 0.3075(3) 0.43717(15) 0.61282(12) 0.0261(4) Uani 1 1 d . . . . .
C007 C 0.3181(3) 0.33289(15) 0.56955(12) 0.0264(4) Uani 1 1 d . . . . .
C008 C 0.1406(3) 0.56011(15) 0.29335(12) 0.0287(4) Uani 1 1 d . . . . .
C009 C 0.3669(3) 0.23959(15) 0.62514(13) 0.0275(4) Uani 1 1 d . . . . .
C00A C 0.1919(3) 0.64941(15) 0.45104(12) 0.0268(4) Uani 1 1 d . . . . .
C00B C 0.1938(3) 0.74343(15) 0.50439(13) 0.0280(4) Uani 1 1 d . . . . .
H00B H 0.221263 0.737892 0.568135 0.034 Uiso 1 1 calc R U . . .
C00C C 0.1498(3) 0.65617(15) 0.35703(12) 0.0276(4) Uani 1 1 d . . . . .
C00D C 0.3418(3) 0.44326(16) 0.70552(13) 0.0305(4) Uani 1 1 d . . . . .
H00D H 0.332614 0.512279 0.733797 0.037 Uiso 1 1 calc R U . . .
C00E C 0.1124(3) 0.75969(16) 0.31819(13) 0.0310(4) Uani 1 1 d . . . . .
H00E H 0.083024 0.766113 0.254564 0.037 Uiso 1 1 calc R U . . .
C00F C 0.3421(3) 0.13103(16) 0.49066(13) 0.0308(4) Uani 1 1 d . . . . .
H00F H 0.349061 0.062920 0.460704 0.037 Uiso 1 1 calc R U . . .
C00G C 0.2944(3) 0.22752(16) 0.44146(13) 0.0299(4) Uani 1 1 d . . . . .
H00G H 0.269171 0.222119 0.377664 0.036 Uiso 1 1 calc R U . . .
C00H C 0.1557(3) 0.84404(16) 0.46427(13) 0.0310(4) Uani 1 1 d . . . . .
H00H H 0.155330 0.907917 0.500377 0.037 Uiso 1 1 calc R U . . .
C00I C 0.1178(3) 0.85217(16) 0.37077(14) 0.0319(4) Uani 1 1 d . . . . .
H00I H 0.095423 0.921933 0.343199 0.038 Uiso 1 1 calc R U . . .
C00J C 0.3783(3) 0.13717(16) 0.58255(13) 0.0309(4) Uani 1 1 d . . . . .
H00J H 0.410926 0.073138 0.617433 0.037 Uiso 1 1 calc R U . . .
C00K C 0.4028(3) 0.25060(16) 0.72015(13) 0.0313(4) Uani 1 1 d . . . . .
H00K H 0.436093 0.188001 0.756739 0.038 Uiso 1 1 calc R U . . .
C00L C 0.3900(3) 0.35059(17) 0.75931(13) 0.0321(4) Uani 1 1 d . . . . .
H00L H 0.413645 0.357462 0.823033 0.039 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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
C008 O001 H001 109.5 . . ?
C00G N003 C007 117.82(16) . . ?
N005 N004 C006 117.09(15) . . ?
N004 N005 C00A 114.57(15) . . ?
N004 C006 C007 128.28(16) . . ?
C00D C006 N004 112.31(16) . . ?
C00D C006 C007 119.41(16) . . ?
N003 C007 C006 120.21(16) . . ?
N003 C007 C009 121.86(17) . . ?
C009 C007 C006 117.93(16) . . ?
O001 C008 C00C 120.00(16) . . ?
O002 C008 O001 119.35(17) . . ?
O002 C008 C00C 120.65(17) . . ?
C00J C009 C007 117.92(17) . . ?
C00J C009 C00K 121.71(17) . . ?
C00K C009 C007 120.37(17) . . ?
C00B C00A N005 122.77(16) . . ?
C00B C00A C00C 120.73(17) . . ?
C00C C00A N005 116.49(16) . . ?
C00A C00B H00B 120.1 . . ?
C00H C00B C00A 119.81(17) . . ?
C00H C00B H00B 120.1 . . ?
C00A C00C C008 125.12(17) . . ?
C00E C00C C008 116.76(16) . . ?
C00E C00C C00A 118.12(17) . . ?
C006 C00D H00D 119.0 . . ?
C006 C00D C00L 121.95(18) . . ?
C00L C00D H00D 119.0 . . ?
C00C C00E H00E 119.5 . . ?
C00I C00E C00C 120.99(18) . . ?
C00I C00E H00E 119.5 . . ?
C00G C00F H00F 120.7 . . ?
C00J C00F H00F 120.7 . . ?
C00J C00F C00G 118.61(18) . . ?
N003 C00G C00F 124.41(17) . . ?
N003 C00G H00G 117.8 . . ?
C00F C00G H00G 117.8 . . ?
C00B C00H H00H 120.0 . . ?
C00B C00H C00I 120.02(17) . . ?
C00I C00H H00H 120.0 . . ?
C00E C00I C00H 120.30(18) . . ?
C00E C00I H00I 119.9 . . ?
C00H C00I H00I 119.9 . . ?
C009 C00J H00J 120.3 . . ?
C00F C00J C009 119.38(17) . . ?
C00F C00J H00J 120.3 . . ?
C009 C00K H00K 119.8 . . ?
C00L C00K C009 120.33(17) . . ?
C00L C00K H00K 119.8 . . ?
C00D C00L H00L 120.0 . . ?
C00K C00L C00D 120.01(17) . . ?
C00K C00L H00L 120.0 . . ?
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
O001 H001 0.8400 . ?
O001 C008 1.327(2) . ?
O002 C008 1.210(2) . ?
N003 C007 1.365(2) . ?
N003 C00G 1.319(2) . ?
N004 N005 1.258(2) . ?
N004 C006 1.412(2) . ?
N005 C00A 1.419(2) . ?
C006 C007 1.436(3) . ?
C006 C00D 1.378(2) . ?
C007 C009 1.424(3) . ?
C008 C00C 1.508(3) . ?
C009 C00J 1.412(3) . ?
C009 C00K 1.417(3) . ?
C00A C00B 1.399(3) . ?
C00A C00C 1.401(3) . ?
C00B H00B 0.9500 . ?
C00B C00H 1.377(3) . ?
C00C C00E 1.401(3) . ?
C00D H00D 0.9500 . ?
C00D C00L 1.402(3) . ?
C00E H00E 0.9500 . ?
C00E C00I 1.375(3) . ?
C00F H00F 0.9500 . ?
C00F C00G 1.405(3) . ?
C00F C00J 1.367(3) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9500 . ?
C00H C00I 1.393(3) . ?
C00I H00I 0.9500 . ?
C00J H00J 0.9500 . ?
C00K H00K 0.9500 . ?
C00K C00L 1.364(3) . ?
C00L H00L 0.9500 . ?
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
O001 C008 C00C C00A -2.4(3) . . . . ?
O001 C008 C00C C00E 177.80(18) . . . . ?
O002 C008 C00C C00A 177.65(19) . . . . ?
O002 C008 C00C C00E -2.2(3) . . . . ?
N003 C007 C009 C00J 0.2(3) . . . . ?
N003 C007 C009 C00K -179.93(17) . . . . ?
N004 N005 C00A C00B 2.8(3) . . . . ?
N004 N005 C00A C00C -177.89(16) . . . . ?
N004 C006 C007 N003 -0.8(3) . . . . ?
N004 C006 C007 C009 179.09(18) . . . . ?
N004 C006 C00D C00L -178.98(18) . . . . ?
N005 N004 C006 C007 -0.9(3) . . . . ?
N005 N004 C006 C00D 179.10(17) . . . . ?
N005 C00A C00B C00H 178.66(18) . . . . ?
N005 C00A C00C C008 1.7(3) . . . . ?
N005 C00A C00C C00E -178.45(17) . . . . ?
C006 N004 N005 C00A -179.93(16) . . . . ?
C006 C007 C009 C00J -179.65(17) . . . . ?
C006 C007 C009 C00K 0.2(3) . . . . ?
C006 C00D C00L C00K -0.4(3) . . . . ?
C007 N003 C00G C00F -0.2(3) . . . . ?
C007 C006 C00D C00L 1.0(3) . . . . ?
C007 C009 C00J C00F -0.2(3) . . . . ?
C007 C009 C00K C00L 0.4(3) . . . . ?
C008 C00C C00E C00I -179.89(18) . . . . ?
C009 C00K C00L C00D -0.3(3) . . . . ?
C00A C00B C00H C00I -0.8(3) . . . . ?
C00A C00C C00E C00I 0.3(3) . . . . ?
C00B C00A C00C C008 -178.95(17) . . . . ?
C00B C00A C00C C00E 0.9(3) . . . . ?
C00B C00H C00I C00E 1.9(3) . . . . ?
C00C C00A C00B C00H -0.6(3) . . . . ?
C00C C00E C00I C00H -1.7(3) . . . . ?
C00D C006 C007 N003 179.26(17) . . . . ?
C00D C006 C007 C009 -0.9(3) . . . . ?
C00G N003 C007 C006 179.83(17) . . . . ?
C00G N003 C007 C009 0.0(3) . . . . ?
C00G C00F C00J C009 0.0(3) . . . . ?
C00J C009 C00K C00L -179.78(18) . . . . ?
C00J C00F C00G N003 0.2(3) . . . . ?
C00K C009 C00J C00F 179.95(18) . . . . ?
