#------------------------------------------------------------------------------
#$Date: 2022-05-19 03:56:26 +0300 (Thu, 19 May 2022) $
#$Revision: 275537 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/49/7244956.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_7244956
loop_
_publ_author_name
'Hawkins, Bryson A.'
'Najib, Elias'
'Du, Jonathan J.'
'Lai, Felcia'
'Platts, James A.'
'Groundwater, Paul W.'
'Hibbs, David E.'
_publ_section_title
;
 Exploring the excited-state charge transfer fluorescence profile of
 7-hydroxycoumarin and 2-methylimidazole -- a combined X-ray diffraction
 and theoretical approach
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D2CP01235A
_journal_year                    2022
_chemical_formula_moiety         'C12 H10 O5, H2 O'
_chemical_formula_sum            'C12 H12 O6'
_chemical_formula_weight         252.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-28 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                103.594(3)
_cell_angle_beta                 96.171(3)
_cell_angle_gamma                98.824(4)
_cell_formula_units_Z            2
_cell_length_a                   6.6514(3)
_cell_length_b                   7.1118(3)
_cell_length_c                   12.5709(3)
_cell_measurement_reflns_used    9367
_cell_measurement_temperature    139(20)
_cell_measurement_theta_max      40.2340
_cell_measurement_theta_min      3.0200
_cell_volume                     564.73(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      139(20)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2474
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  28.20   0.30    7.50    --    1.09 -57.00-180.00  334
  2  ω    -11.00  91.00   0.30    7.50    --   18.00  60.00  13.45  340
  3  ω     -3.00  99.00   0.30    7.50    --   26.00  59.00 119.13  340
  4  ω      2.00 102.20   0.30    7.50    --   30.00  58.00 -88.60  334
  5  ω    -34.00  66.20   0.30   30.00    --   38.00 -59.00 -41.19  334
  6  ω   -135.00 -34.80   0.30   30.00    --  -62.64 -59.00-156.86  334
  7  ω    -92.00  10.00   0.30   30.00    --  -62.64  60.00-179.79  340
  8  ω   -135.00 -34.80   0.30   30.00    --  -62.64 -58.00-126.98  334
  9  ω   -135.00 -34.80   0.30   30.00    --  -62.64 -57.00 -90.00  334
 10  ω    -92.00  10.00   0.30   30.00    --  -62.64  60.00 -37.36  340
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0224651000
_diffrn_orient_matrix_UB_12      0.0915057000
_diffrn_orient_matrix_UB_13      0.0405010000
_diffrn_orient_matrix_UB_21      0.0093786000
_diffrn_orient_matrix_UB_22      -0.0500422000
_diffrn_orient_matrix_UB_23      0.0423758000
_diffrn_orient_matrix_UB_31      0.1063921000
_diffrn_orient_matrix_UB_32      0.0048929000
_diffrn_orient_matrix_UB_33      -0.0032862000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12124
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.999
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.773
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.551
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.139
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0347
_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)+(0.0639P)²+0.1208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2461
_reflns_number_total             2799
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cp01235a2.cif
_cod_data_source_block           21bh011_cd_c
_cod_database_code               7244956
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C11 H10 N O'
_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.
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
;
_olex2_submission_original_sample_id EN09-hydrate
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.541
_oxdiff_exptl_absorpt_empirical_full_min 0.726
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O4 O 0.82431(10) 0.29226(11) 0.52823(6) 0.01738(17) Uani 1 1 d . . . . .
O1 O 0.43707(11) 0.18946(11) 0.81047(6) 0.01763(18) Uani 1 1 d . . . . .
O2 O 0.76966(11) 0.32864(12) 0.86877(6) 0.02081(19) Uani 1 1 d . . . . .
O5 O 0.49143(13) 0.30314(13) 0.17674(6) 0.0244(2) Uani 1 1 d . . . . .
O3 O 0.99627(11) 0.30765(13) 0.69039(6) 0.0233(2) Uani 1 1 d . . . . .
O1' O 0.84356(13) 0.39638(13) 0.10914(7) 0.0259(2) Uani 1 1 d . . . . .
C7 C 0.45462(15) 0.24061(14) 0.49343(8) 0.0146(2) Uani 1 1 d . . . . .
C8 C 0.45154(15) 0.23388(14) 0.60561(8) 0.0146(2) Uani 1 1 d . . . . .
C3 C 0.62424(15) 0.26369(14) 0.79491(8) 0.0148(2) Uani 1 1 d . . . . .
C9 C 0.66627(16) 0.29586(15) 0.35240(8) 0.0171(2) Uani 1 1 d . . . . .
C4 C 0.62896(15) 0.25914(14) 0.67645(8) 0.0146(2) Uani 1 1 d . . . . .
C11 C 0.29259(16) 0.23834(16) 0.31137(9) 0.0193(2) Uani 1 1 d . . . . .
C6 C 0.64588(14) 0.27510(14) 0.45794(8) 0.0148(2) Uani 1 1 d . . . . .
C5 C 0.82763(15) 0.28829(15) 0.63820(8) 0.0161(2) Uani 1 1 d . . . . .
C12 C 0.27625(15) 0.22116(15) 0.41709(8) 0.0174(2) Uani 1 1 d . . . . .
C10 C 0.48759(16) 0.27871(15) 0.27937(8) 0.0178(2) Uani 1 1 d . . . . .
C2 C 0.40804(16) 0.19819(16) 0.92453(8) 0.0177(2) Uani 1 1 d . . . . .
C1 C 0.18990(17) 0.10242(18) 0.92278(9) 0.0230(2) Uani 1 1 d . . . . .
H1A H 0.092(3) 0.163(3) 0.8841(14) 0.039(4) Uiso 1 1 d . . . . .
H1B H 0.161(2) 0.118(2) 1.0009(13) 0.034(4) Uiso 1 1 d . . . . .
H1C H 0.167(2) -0.040(2) 0.8861(12) 0.024(3) Uiso 1 1 d . . . . .
H1'A H 0.830(3) 0.381(3) 0.0400(17) 0.047(5) Uiso 1 1 d . . . . .
H1'B H 0.932(3) 0.494(3) 0.1409(16) 0.046(5) Uiso 1 1 d . . . . .
H2A H 0.508(2) 0.128(2) 0.9558(11) 0.022(3) Uiso 1 1 d . . . . .
H2B H 0.434(2) 0.338(2) 0.9644(11) 0.019(3) Uiso 1 1 d . . . . .
H12 H 0.142(2) 0.198(2) 0.4408(12) 0.022(3) Uiso 1 1 d . . . . .
H9 H 0.801(2) 0.322(2) 0.3313(13) 0.032(4) Uiso 1 1 d . . . . .
H11 H 0.175(2) 0.227(2) 0.2603(12) 0.026(3) Uiso 1 1 d . . . . .
H8 H 0.323(2) 0.215(2) 0.6333(11) 0.020(3) Uiso 1 1 d . . . . .
H5 H 0.615(4) 0.340(3) 0.1657(18) 0.064(6) Uiso 1 1 d . . . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
9 -1 -3 0.2835
0 10 -3 0.0672
1 -9 -3 0.0612
0 9 3 0.0639
2 -7 -9 0.0620
-4 7 9 0.1275
-9 1 3 0.2491
2 -2 -16 0.0700
-7 2 12 0.1853
-8 0 10 0.2134
2 4 -17 0.0732
-3 -6 15 0.1341
1 10 -8 0.0714
2 9 -8 0.1000
-1 -10 8 0.0746
0 7 8 0.0640
1 -7 -8 0.0592
0 2 16 0.0623
1 -2 -16 0.0596
1 1 -18 0.0612
0 -1 17 0.0639
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
C6 O4 C5 122.99(8) . . ?
C3 O1 C2 116.24(8) . . ?
C10 O5 H5 111.5(15) . . ?
H1'A O1' H1'B 110.9(19) . . ?
C6 C7 C8 118.06(9) . . ?
C6 C7 C12 118.08(9) . . ?
C12 C7 C8 123.83(9) . . ?
C7 C8 H8 120.2(8) . . ?
C4 C8 C7 121.26(9) . . ?
C4 C8 H8 118.5(8) . . ?
O1 C3 C4 110.77(8) . . ?
O2 C3 O1 123.92(9) . . ?
O2 C3 C4 125.30(9) . . ?
C6 C9 C10 117.97(9) . . ?
C6 C9 H9 120.4(9) . . ?
C10 C9 H9 121.7(9) . . ?
C8 C4 C3 120.77(9) . . ?
C8 C4 C5 120.51(9) . . ?
C5 C4 C3 118.69(8) . . ?
C12 C11 C10 120.15(9) . . ?
C12 C11 H11 121.0(9) . . ?
C10 C11 H11 118.8(9) . . ?
O4 C6 C7 120.53(8) . . ?
O4 C6 C9 116.81(8) . . ?
C9 C6 C7 122.65(9) . . ?
O4 C5 C4 116.53(8) . . ?
O3 C5 O4 115.58(9) . . ?
O3 C5 C4 127.88(9) . . ?
C7 C12 H12 118.9(8) . . ?
C11 C12 C7 120.30(9) . . ?
C11 C12 H12 120.7(8) . . ?
O5 C10 C9 122.42(10) . . ?
O5 C10 C11 116.74(9) . . ?
C9 C10 C11 120.82(9) . . ?
O1 C2 C1 107.39(8) . . ?
O1 C2 H2A 108.2(8) . . ?
O1 C2 H2B 107.0(8) . . ?
C1 C2 H2A 111.7(8) . . ?
C1 C2 H2B 111.2(8) . . ?
H2A C2 H2B 111.1(11) . . ?
C2 C1 H1A 111.5(10) . . ?
C2 C1 H1B 109.1(9) . . ?
C2 C1 H1C 110.9(8) . . ?
H1A C1 H1B 108.4(13) . . ?
H1A C1 H1C 108.7(13) . . ?
H1B C1 H1C 108.1(12) . . ?
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
O4 C6 1.3725(12) . ?
O4 C5 1.3872(11) . ?
O1 C3 1.3290(12) . ?
O1 C2 1.4555(11) . ?
O2 C3 1.2162(12) . ?
O5 C10 1.3440(12) . ?
O5 H5 0.86(2) . ?
O3 C5 1.2082(12) . ?
O1' H1'A 0.84(2) . ?
O1' H1'B 0.83(2) . ?
C7 C8 1.4245(13) . ?
C7 C6 1.3983(13) . ?
C7 C12 1.4107(13) . ?
C8 C4 1.3608(13) . ?
C8 H8 0.959(14) . ?
C3 C4 1.4857(13) . ?
C9 C6 1.3874(13) . ?
C9 C10 1.3923(14) . ?
C9 H9 0.966(16) . ?
C4 C5 1.4560(13) . ?
C11 C12 1.3771(14) . ?
C11 C10 1.4067(15) . ?
C11 H11 0.937(15) . ?
C12 H12 0.971(14) . ?
C2 C1 1.5008(14) . ?
C2 H2A 0.995(14) . ?
C2 H2B 0.981(14) . ?
C1 H1A 0.981(17) . ?
C1 H1B 1.004(16) . ?
C1 H1C 0.988(15) . ?
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
O1 C3 C4 C8 16.72(13) . . . . ?
O1 C3 C4 C5 -165.14(9) . . . . ?
O2 C3 C4 C8 -162.26(10) . . . . ?
O2 C3 C4 C5 15.88(15) . . . . ?
C7 C8 C4 C3 176.33(8) . . . . ?
C7 C8 C4 C5 -1.77(15) . . . . ?
C8 C7 C6 O4 3.09(14) . . . . ?
C8 C7 C6 C9 -176.14(9) . . . . ?
C8 C7 C12 C11 177.01(9) . . . . ?
C8 C4 C5 O4 1.16(14) . . . . ?
C8 C4 C5 O3 -178.03(10) . . . . ?
C3 O1 C2 C1 -178.46(9) . . . . ?
C3 C4 C5 O4 -176.98(8) . . . . ?
C3 C4 C5 O3 3.83(16) . . . . ?
C6 O4 C5 O3 -179.07(9) . . . . ?
C6 O4 C5 C4 1.64(14) . . . . ?
C6 C7 C8 C4 -0.34(15) . . . . ?
C6 C7 C12 C11 -0.76(15) . . . . ?
C6 C9 C10 O5 177.67(9) . . . . ?
C6 C9 C10 C11 -1.03(16) . . . . ?
C5 O4 C6 C7 -3.82(15) . . . . ?
C5 O4 C6 C9 175.45(9) . . . . ?
C12 C7 C8 C4 -178.11(9) . . . . ?
C12 C7 C6 O4 -179.01(8) . . . . ?
C12 C7 C6 C9 1.76(15) . . . . ?
C12 C11 C10 O5 -176.77(9) . . . . ?
C12 C11 C10 C9 1.99(16) . . . . ?
C10 C9 C6 O4 179.88(9) . . . . ?
C10 C9 C6 C7 -0.87(16) . . . . ?
C10 C11 C12 C7 -1.06(16) . . . . ?
C2 O1 C3 O2 3.21(14) . . . . ?
C2 O1 C3 C4 -175.79(8) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
9.3508 -0.9732 -3.0038 -0.0006 0.0091 1.0000
-0.4502 9.9123 -2.5489 0.7937 -0.6083 0.0090
1.4928 -9.1257 -3.3076 -0.9355 0.3305 0.1250
-0.2434 9.0759 2.9079 0.9428 -0.3332 0.0090
1.9790 -7.3881 -8.5765 -0.9789 0.0248 0.2026
-4.0862 7.0330 8.6747 0.9031 -0.0227 -0.4288
-9.3435 0.9644 3.2252 0.0090 0.0008 -1.0000
2.1671 -2.1543 -15.9020 -0.7925 -0.5457 0.2723
-6.9700 1.9520 12.3575 0.5225 0.3606 -0.7726
-8.1807 0.3181 10.2663 0.2611 0.3424 -0.9025
1.7332 3.7702 -17.4175 -0.3215 -0.9105 0.2601
-3.4428 -5.6500 15.2282 0.0224 0.8958 -0.4440
0.7359 9.5361 -8.1146 0.5605 -0.8142 0.1516
2.1709 9.0541 -8.3125 0.5406 -0.7850 0.3026
-0.6700 -9.5526 8.1009 -0.5611 0.8150 -0.1446
0.3045 7.3138 7.9676 0.9988 -0.0255 0.0420
0.9496 -7.4114 -8.3592 -0.9954 0.0256 0.0922
0.3056 1.9941 15.6644 0.8238 0.5669 -0.0092
0.9832 -2.0984 -15.9262 -0.8150 -0.5607 0.1467
0.7569 0.9931 -17.5309 -0.6021 -0.7855 0.1430
0.4996 -1.1271 17.2880 0.6083 0.7937 -0.0092
