# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pag19_s1966_sq
_database_code_depnum_ccdc_archive 'CCDC 1999498'
loop_
_audit_author_name
_audit_author_address
'William Lewis'
;The University of Sydney
Australia
;
_audit_update_record             
;
2020-04-27 deposited with the CCDC.	2023-02-24 downloaded from the CCDC.
;
_sydney_internal_submission_code pag19_s1966
_sydney_internal_submission_date 2019-12-11
_sydney_internal_submission_number s1966
_sydney_internal_client_code     mmet
_sydney_internal_client_email    'Mohamed Metwaly'
_sydney_internal_client_name     mmet5356@chem.usyd.edu.au
_sydney_internal_supervisor_code pag
_sydney_internal_supervisor_name 'Phil Gale'
_sydney_internal_collection_date 2019-12-19
_sydney_internal_collection_user wlew0588
_sydney_internal_process_date    2020-01-13
_sydney_internal_process_user    wlew0588
_sydney_internal_solution_date   2020-01-13
_sydney_internal_solution_user   wlew0588
_sydney_internal_refine_date     2020-01-13
_sydney_internal_refine_user     wlew0588
_sydney_internal_check_and_archive_date 2020-01-13
_sydney_internal_check_user      wlew0588
_refine_special_details          
;
The methyl coumarine is rotationally disorder about its long axis, with common 
positions for the two terminal carbon atoms attached to the urea groups. The 
occupanices of two components were refined competitively, converging to a ratio 
of 0.72:0.28. The disordered atoms were restrained to have approximately similar 
bond legnths and angles for equivalent atoms, and the bonds of the two terminal 
carbon atoms to disordered carbon atoms were restrained to be approxiamtely equal. 

There is a are of continuous electron density along the c-axis, centred at the 
middle of the unit cell. This could not be sensibly refined, so the structure 
was treated with PLATON SQUEEZE, which calculated 114 electrons per cell for this 
void. The was assigned as 4 molecules of ethanol, accounting for 104 electrons. This 
region is likely disordered due to the adjacent disordered coumarine, which 
should be acting as a hydrogen bond acceptor to the ethanol molecules in this void. 
Disorder of the coumarine has resulted in ethanol molecules that are too 
disordered to locate.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.500 -0.038 560 113 '4 C2H6O'

_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
_platon_squeeze_special_details  ?
_audit_creation_date             2020-01-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 N4 O4, 1[C2H6O]'
_chemical_formula_sum            'C26 H26 N4 O5'
_chemical_formula_weight         474.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H20N4O4
_chemical_oxdiff_usercomment     HBisUreaCoumarine
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   28.2772(10)
_cell_length_b                   11.1135(9)
_cell_length_c                   7.9823(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.234(4)
_cell_angle_gamma                90
_cell_volume                     2508.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2046
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.5320
_cell_measurement_theta_min      3.9560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.568
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0039
-1 0 0 0.0029
0 1 0 0.0138
0 -1 0 0.0048
0 0 1 0.2275
0 0 -1 0.2045

_exptl_crystal_recrystallization_method 
'crystallised from a mixture of dimethylformamide and ethanol'
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.019
_exptl_crystal_size_min          0.007
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
0.9989 -0.0005 -0.0001 -0.0050 -0.0537 -0.0075
-0.9989 0.0005 0.0001 0.0050 0.0537 0.0075
0.0041 1.0015 0.0015 -0.1381 0.0118 0.0078
-0.0041 -1.0015 -0.0015 0.1381 -0.0118 -0.0078
0.0031 -0.0025 1.0006 -0.0086 0.0265 -0.1911
-0.0031 0.0025 -1.0006 0.0086 -0.0265 0.1911

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_unetI/netI     0.0957
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            19257
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.655
_diffrn_reflns_theta_min         3.978
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.5861
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  41.00   1.00   30.00    --  -38.19  19.00-150.00   44
  2  ω    -26.00  58.00   1.00   30.00    --   38.19 -38.00   0.00   84
  3  ω     91.00 119.00   1.00   30.00    --   38.19 178.00 -30.00   28
  4  ω     29.00  57.00   1.00  120.00    --  107.32 -30.00   0.00   28
  5  ω     28.00  54.00   1.00  120.00    --  107.32 -30.00  30.00   26
  6  ω     28.00  57.00   1.00  120.00    --  107.32 -30.00 120.00   29
  7  ω     94.00 133.00   1.00  120.00    --  107.32  45.00-150.00   39
  8  ω     43.00  69.00   1.00  120.00    --  107.32 -45.00 -60.00   26
  9  ω     24.00 102.00   1.00  120.00    --  107.32 -95.00 -60.00   78
 10  ω    135.00 160.00   1.00  120.00    --  107.32  45.00-150.00   25
 11  ω    135.00 165.00   1.00  120.00    --  107.32 111.00 150.00   30
 12  ω    -64.00 -39.00   1.00   30.00    --  -38.32-178.00  30.00   25
 13  ω   -128.00-102.00   1.00   30.00    --  -38.32-178.00  30.00   26
 14  ω    -90.00 -37.00   1.00   30.00    --  -38.32 178.00 150.00   53
 15  ω     29.00  56.00   1.00  120.00    --  107.32 -30.00-150.00   27
 16  ω     57.00 109.00   1.00  120.00    --  107.32-111.00  30.00   52
 17  ω     29.00  56.00   1.00  120.00    --  107.32 -30.00  60.00   27
 18  ω     31.00  57.00   1.00  120.00    --  107.32 -30.00  90.00   26
 19  ω     28.00  53.00   1.00  120.00    --  107.32 -30.00 -60.00   25
 20  ω    124.00 161.00   1.00  120.00    --  107.32 144.00-158.00   37
 21  ω     38.00  64.00   1.00  120.00    --  107.32 -45.00 -90.00   26
 22  ω     73.00  99.00   1.00  120.00    --  107.32  30.00-120.00   26
 23  ω    113.00 163.00   1.00  120.00    --  107.32  30.00-120.00   50
 24  ω     55.00  81.00   1.00  120.00    --  107.32 -61.00   0.00   26
 25  ω     -5.00  20.00   1.00   30.00    --  -39.07  19.00-120.00   25
 26  ω     79.00 105.00   1.00  120.00    --  107.94-111.00  60.00   26
 27  ω     31.00  56.00   1.00  120.00    --  107.94 -45.00-180.00   25
 28  ω   -115.00  -8.00   1.00   30.00    --  -39.07 -57.00 120.00  107
 29  ω    -21.00  38.00   1.00   30.00    --  -39.07  38.00   0.00   59
 30  ω   -115.00  -8.00   1.00   30.00    --  -39.07 -57.00 -90.00  107
 31  ω   -115.00  -8.00   1.00   30.00    --  -39.07 -57.00-180.00  107
 32  ω    -21.00  38.00   1.00   30.00    --  -39.07  38.00 150.00   59
 33  ω   -115.00  -8.00   1.00   30.00    --  -39.07 -57.00  30.00  107
 34  ω     75.00 121.00   1.00   30.00    --   39.07 161.00  99.00   46
 35  ω     31.00  56.00   1.00  120.00    --  107.94  15.00 120.00   25
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0051107000
_diffrn_orient_matrix_UB_12      -0.1378192000
_diffrn_orient_matrix_UB_13      -0.0089305000
_diffrn_orient_matrix_UB_21      -0.0537282000
_diffrn_orient_matrix_UB_22      0.0119977000
_diffrn_orient_matrix_UB_23      0.0266831000
_diffrn_orient_matrix_UB_31      -0.0075212000
_diffrn_orient_matrix_UB_32      0.0080829000
_diffrn_orient_matrix_UB_33      -0.1909596000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2100
_reflns_number_total             4894
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.00081(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         4894
_refine_ls_number_restraints     855
_refine_ls_R_factor_all          0.1531
_refine_ls_R_factor_gt           0.0661
_refine_ls_restrained_S_all      0.889
_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)+(0.0884P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1579
_refine_ls_wR_factor_ref         0.2088
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C8-C6A \\sim C9-C8 \\sim C7-C6 \\sim C9A-C7
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{O1, C2, C3, C4, C5, C6, C9, C10, O11, C12} sigma for 1-2: 0.02, 1-3: 0.04
as in
{O1A, C2A, C3A, C4A, C5A, C6A, C9A, C10A, O11A, C12A}
6. Others
 Sof(O1A)=Sof(C2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(C5A)=Sof(C6A)=Sof(H6A)=
 Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(O11A)=Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=
 1-FVAR(1)
 Sof(O1)=Sof(C2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C5)=Sof(C6)=Sof(H6)=Sof(C9)=
 Sof(H9)=Sof(C10)=Sof(O11)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C9(H9), N13(H13), N15(H15), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), N23(H23), N25(H25), C28(H28), C29(H29), C30(H30), C31(H31),
  C32(H32), C3A(H3A), C6A(H6A), C9A(H9A)
7.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C12A(H12D,H12E,H12F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.40463(14) 0.1535(5) 0.7673(6) 0.0729(11) Uani 0.725(4) 1 d D U P A 1
C2 C 0.4432(2) 0.1029(8) 0.8478(9) 0.0752(13) Uani 0.725(4) 1 d D U P A 1
C3 C 0.4470(3) -0.0246(8) 0.8474(11) 0.0737(12) Uani 0.725(4) 1 d D U P A 1
H3 H 0.473429 -0.060478 0.901892 0.088 Uiso 0.725(4) 1 calc R U P A 1
C4 C 0.4153(2) -0.0963(8) 0.7742(9) 0.0704(12) Uani 0.725(4) 1 d D U P A 1
C5 C 0.3744(3) -0.0423(9) 0.6932(14) 0.0654(11) Uani 0.725(4) 1 d D U P A 1
C6 C 0.3379(2) -0.1103(9) 0.6168(14) 0.0631(13) Uani 0.725(4) 1 d D U P A 1
H6 H 0.340253 -0.195599 0.614558 0.076 Uiso 0.725(4) 1 calc R U P A 1
C9 C 0.3326(3) 0.1396(9) 0.6181(17) 0.0650(13) Uani 0.725(4) 1 d D U P A 1
H9 H 0.330369 0.224876 0.619111 0.078 Uiso 0.725(4) 1 calc R U P A 1
C10 C 0.3703(3) 0.0802(9) 0.6926(15) 0.0663(12) Uani 0.725(4) 1 d D U P A 1
O11 O 0.47010(14) 0.1731(5) 0.9151(6) 0.0930(15) Uani 0.725(4) 1 d D U P A 1
C12 C 0.4195(2) -0.2311(7) 0.7795(8) 0.0831(17) Uani 0.725(4) 1 d D U P A 1
H12A H 0.447969 -0.253665 0.842601 0.125 Uiso 0.725(4) 1 calc R U P A 1
H12B H 0.421706 -0.262523 0.665061 0.125 Uiso 0.725(4) 1 calc R U P A 1
H12C H 0.391593 -0.265130 0.834336 0.125 Uiso 0.725(4) 1 calc R U P A 1
C7 C 0.29877(12) -0.0553(5) 0.5452(4) 0.0611(9) Uani 1 1 d D U . . .
C8 C 0.29801(13) 0.0688(5) 0.5419(4) 0.0623(9) Uani 1 1 d D U . . .
N13 N 0.26014(10) -0.1201(3) 0.4734(4) 0.0587(9) Uani 1 1 d . U . . .
H13 H 0.264751 -0.169274 0.388581 0.070 Uiso 1 1 calc R U . . .
C14 C 0.21594(13) -0.1047(4) 0.5379(4) 0.0537(9) Uani 1 1 d . U . . .
N15 N 0.18012(10) -0.1527(3) 0.4454(3) 0.0505(8) Uani 1 1 d . U . . .
H15 H 0.188040 -0.193027 0.354957 0.061 Uiso 1 1 calc R U . . .
O16 O 0.20944(8) -0.0526(3) 0.6720(3) 0.0568(8) Uani 1 1 d . U . . .
C17 C 0.13137(12) -0.1436(4) 0.4811(4) 0.0440(8) Uani 1 1 d . U . . .
C18 C 0.10140(12) -0.2275(4) 0.4097(4) 0.0483(9) Uani 1 1 d . U . . .
H18 H 0.114018 -0.289047 0.340473 0.058 Uiso 1 1 calc R U . . .
C19 C 0.05321(13) -0.2226(4) 0.4378(5) 0.0492(9) Uani 1 1 d . U . . .
H19 H 0.033001 -0.281005 0.388229 0.059 Uiso 1 1 calc R U . . .
C20 C 0.03424(13) -0.1331(4) 0.5380(4) 0.0469(9) Uani 1 1 d . U . . .
H20 H 0.001219 -0.130335 0.559126 0.056 Uiso 1 1 calc R U . . .
C21 C 0.06421(13) -0.0477(4) 0.6069(4) 0.0469(8) Uani 1 1 d . U . . .
H21 H 0.051502 0.014182 0.675257 0.056 Uiso 1 1 calc R U . . .
C22 C 0.11271(13) -0.0512(4) 0.5774(4) 0.0456(8) Uani 1 1 d . U . . .
H22 H 0.132832 0.009114 0.622836 0.055 Uiso 1 1 calc R U . . .
N23 N 0.26069(10) 0.1276(4) 0.4566(4) 0.0612(9) Uani 1 1 d . U . . .
H23 H 0.257257 0.114316 0.348507 0.073 Uiso 1 1 calc R U . . .
C24 C 0.22984(13) 0.2034(4) 0.5327(4) 0.0579(10) Uani 1 1 d . U . . .
N25 N 0.18952(10) 0.2253(3) 0.4413(3) 0.0537(8) Uani 1 1 d . U . . .
H25 H 0.186528 0.186025 0.346110 0.064 Uiso 1 1 calc R U . . .
O26 O 0.23696(9) 0.2491(3) 0.6722(3) 0.0597(8) Uani 1 1 d . U . . .
C27 C 0.15250(14) 0.3038(4) 0.4840(4) 0.0520(9) Uani 1 1 d . U . . .
C28 C 0.10724(13) 0.2757(4) 0.4296(5) 0.0515(9) Uani 1 1 d . U . . .
H28 H 0.101770 0.203751 0.368193 0.062 Uiso 1 1 calc R U . . .
C29 C 0.07015(14) 0.3521(4) 0.4646(5) 0.0563(10) Uani 1 1 d . U . . .
H29 H 0.039249 0.332387 0.426278 0.068 Uiso 1 1 calc R U . . .
C30 C 0.07726(17) 0.4571(4) 0.5547(5) 0.0632(10) Uani 1 1 d . U . . .
H30 H 0.051559 0.508919 0.580301 0.076 Uiso 1 1 calc R U . . .
C31 C 0.12259(17) 0.4845(4) 0.6064(5) 0.0672(11) Uani 1 1 d . U . . .
H31 H 0.128064 0.556689 0.667198 0.081 Uiso 1 1 calc R U . . .
C32 C 0.16004(16) 0.4097(4) 0.5719(5) 0.0615(10) Uani 1 1 d . U . . .
H32 H 0.191006 0.430603 0.608141 0.074 Uiso 1 1 calc R U . . .
O1A O 0.4044(4) -0.1458(14) 0.7681(17) 0.0702(15) Uani 0.275(4) 1 d D U P A 2
C2A C 0.4434(5) -0.0970(15) 0.850(2) 0.0727(16) Uani 0.275(4) 1 d D U P A 2
C3A C 0.4463(7) 0.0323(15) 0.848(3) 0.0735(14) Uani 0.275(4) 1 d D U P A 2
H3A H 0.472254 0.069124 0.903985 0.088 Uiso 0.275(4) 1 calc R U P A 2
C4A C 0.4147(6) 0.1038(16) 0.772(3) 0.0726(14) Uani 0.275(4) 1 d D U P A 2
C5A C 0.3734(8) 0.0491(18) 0.696(4) 0.0671(13) Uani 0.275(4) 1 d D U P A 2
C6A C 0.3380(8) 0.120(2) 0.617(5) 0.0651(16) Uani 0.275(4) 1 d D U P A 2
H6A H 0.341569 0.205354 0.615440 0.078 Uiso 0.275(4) 1 calc R U P A 2
C9A C 0.3313(7) -0.134(2) 0.619(4) 0.0635(16) Uani 0.275(4) 1 d D U P A 2
H9A H 0.327653 -0.218486 0.620686 0.076 Uiso 0.275(4) 1 calc R U P A 2
C10A C 0.3696(8) -0.0734(19) 0.691(4) 0.0665(13) Uani 0.275(4) 1 d D U P A 2
O11A O 0.4704(3) -0.1669(12) 0.9205(14) 0.085(2) Uani 0.275(4) 1 d D U P A 2
C12A C 0.4185(6) 0.2405(16) 0.777(2) 0.086(3) Uani 0.275(4) 1 d D U P A 2
H12D H 0.443496 0.264016 0.855592 0.128 Uiso 0.275(4) 1 calc R U P A 2
H12E H 0.388264 0.274563 0.813602 0.128 Uiso 0.275(4) 1 calc R U P A 2
H12F H 0.426021 0.270861 0.664891 0.128 Uiso 0.275(4) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C2 1.384(7) . ?
O1 C10 1.398(9) . ?
C2 C3 1.421(10) . ?
C2 O11 1.214(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.332(9) . ?
C4 C5 1.452(10) . ?
C4 C12 1.504(11) . ?
C5 C6 1.416(10) . ?
C5 C10 1.367(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(10) . ?
C9 C8 1.392(8) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C7 C8 1.380(6) . ?
C7 N13 1.426(5) . ?
C7 C9A 1.394(14) . ?
C8 N23 1.413(5) . ?
C8 C6A 1.401(14) . ?
N13 H13 0.8800 . ?
N13 C14 1.365(4) . ?
C14 N15 1.360(4) . ?
C14 O16 1.232(4) . ?
N15 H15 0.8800 . ?
N15 C17 1.412(4) . ?
C17 C18 1.381(5) . ?
C17 C22 1.388(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.393(5) . ?
C22 H22 0.9500 . ?
N23 H23 0.8800 . ?
N23 C24 1.358(5) . ?
C24 N25 1.373(4) . ?
C24 O26 1.240(4) . ?
N25 H25 0.8800 . ?
N25 C27 1.406(5) . ?
C27 C28 1.386(5) . ?
C27 C32 1.386(6) . ?
C28 H28 0.9500 . ?
C28 C29 1.379(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.386(6) . ?
C30 H30 0.9500 . ?
C30 C31 1.379(6) . ?
C31 H31 0.9500 . ?
C31 C32 1.375(6) . ?
C32 H32 0.9500 . ?
O1A C2A 1.388(14) . ?
O1A C10A 1.410(18) . ?
C2A C3A 1.440(17) . ?
C2A O11A 1.226(14) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.340(16) . ?
C4A C5A 1.449(18) . ?
C4A C12A 1.523(18) . ?
C5A C6A 1.419(19) . ?
C5A C10A 1.367(15) . ?
C6A H6A 0.9500 . ?
C9A H9A 0.9500 . ?
C9A C10A 1.394(18) . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?

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
C2 O1 C10 120.3(7) . . ?
O1 C2 C3 117.7(6) . . ?
O11 C2 O1 115.8(7) . . ?
O11 C2 C3 126.5(6) . . ?
C2 C3 H3 118.4 . . ?
C4 C3 C2 123.1(7) . . ?
C4 C3 H3 118.4 . . ?
C3 C4 C5 118.8(8) . . ?
C3 C4 C12 122.0(7) . . ?
C5 C4 C12 119.1(6) . . ?
C6 C5 C4 123.3(8) . . ?
C10 C5 C4 118.7(7) . . ?
C10 C5 C6 117.9(8) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.5(8) . . ?
C7 C6 H6 119.3 . . ?
C10 C9 H9 121.4 . . ?
C10 C9 C8 117.2(9) . . ?
C8 C9 H9 121.4 . . ?
C5 C10 O1 121.4(7) . . ?
C5 C10 C9 122.7(8) . . ?
C9 C10 O1 115.9(8) . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C7 N13 123.5(6) . . ?
C8 C7 C6 117.5(5) . . ?
C8 C7 N13 119.0(4) . . ?
C8 C7 C9A 129.9(10) . . ?
C9A C7 N13 111.0(10) . . ?
C9 C8 N23 118.1(6) . . ?
C7 C8 C9 123.0(6) . . ?
C7 C8 N23 118.9(4) . . ?
C7 C8 C6A 112.8(11) . . ?
C6A C8 N23 128.2(11) . . ?
C7 N13 H13 120.5 . . ?
C14 N13 C7 119.1(3) . . ?
C14 N13 H13 120.5 . . ?
N15 C14 N13 115.3(3) . . ?
O16 C14 N13 121.8(3) . . ?
O16 C14 N15 122.9(3) . . ?
C14 N15 H15 117.0 . . ?
C14 N15 C17 126.0(3) . . ?
C17 N15 H15 117.0 . . ?
C18 C17 N15 117.8(3) . . ?
C18 C17 C22 119.6(3) . . ?
C22 C17 N15 122.5(3) . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.7(4) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(4) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.9(3) . . ?
C21 C20 H20 120.6 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.1(4) . . ?
C22 C21 H21 119.5 . . ?
C17 C22 C21 119.4(4) . . ?
C17 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C8 N23 H23 118.3 . . ?
C24 N23 C8 123.4(3) . . ?
C24 N23 H23 118.3 . . ?
N23 C24 N25 113.9(3) . . ?
O26 C24 N23 123.6(4) . . ?
O26 C24 N25 122.4(4) . . ?
C24 N25 H25 116.6 . . ?
C24 N25 C27 126.8(3) . . ?
C27 N25 H25 116.6 . . ?
C28 C27 N25 118.1(4) . . ?
C32 C27 N25 122.5(4) . . ?
C32 C27 C28 119.4(4) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 120.0(4) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 119.5 . . ?
C28 C29 C30 121.0(4) . . ?
C30 C29 H29 119.5 . . ?
C29 C30 H30 120.8 . . ?
C31 C30 C29 118.3(4) . . ?
C31 C30 H30 120.8 . . ?
C30 C31 H31 119.3 . . ?
C32 C31 C30 121.5(4) . . ?
C32 C31 H31 119.3 . . ?
C27 C32 H32 120.1 . . ?
C31 C32 C27 119.8(4) . . ?
C31 C32 H32 120.1 . . ?
C2A O1A C10A 122.2(14) . . ?
O1A C2A C3A 115.6(14) . . ?
O11A C2A O1A 117.4(15) . . ?
O11A C2A C3A 126.9(14) . . ?
C2A C3A H3A 118.1 . . ?
C4A C3A C2A 123.9(16) . . ?
C4A C3A H3A 118.1 . . ?
C3A C4A C5A 118.5(16) . . ?
C3A C4A C12A 122.2(15) . . ?
C5A C4A C12A 119.0(13) . . ?
C6A C5A C4A 121.1(15) . . ?
C10A C5A C4A 119.5(16) . . ?
C10A C5A C6A 119.3(18) . . ?
C8 C6A C5A 121.8(18) . . ?
C8 C6A H6A 119.1 . . ?
C5A C6A H6A 119.1 . . ?
C7 C9A H9A 123.7 . . ?
C10A C9A C7 112.7(16) . . ?
C10A C9A H9A 123.7 . . ?
C5A C10A O1A 120.1(16) . . ?
C5A C10A C9A 123.3(18) . . ?
C9A C10A O1A 116.5(15) . . ?
C4A C12A H12D 109.5 . . ?
C4A C12A H12E 109.5 . . ?
C4A C12A H12F 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?

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
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N13 H13 O26 0.88 2.09 2.872(4) 147.3 4 yes
N15 H15 O26 0.88 2.11 2.918(4) 152.7 4 yes
N23 H23 O16 0.88 2.07 2.815(4) 142.5 4 yes
N25 H25 O16 0.88 2.13 2.938(4) 151.4 4 yes

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 C2 C3 C4 -0.2(10) . . . . ?
C2 O1 C10 C5 -1.6(13) . . . . ?
C2 O1 C10 C9 178.7(9) . . . . ?
C2 C3 C4 C5 -1.1(12) . . . . ?
C2 C3 C4 C12 -178.3(7) . . . . ?
C3 C4 C5 C6 -177.8(10) . . . . ?
C3 C4 C5 C10 1.1(13) . . . . ?
C4 C5 C6 C7 178.1(9) . . . . ?
C4 C5 C10 O1 0.3(14) . . . . ?
C4 C5 C10 C9 179.9(11) . . . . ?
C5 C6 C7 C8 3.9(12) . . . . ?
C5 C6 C7 N13 -177.2(7) . . . . ?
C6 C5 C10 O1 179.2(10) . . . . ?
C6 C5 C10 C9 -1.2(16) . . . . ?
C6 C7 C8 C9 -5.2(11) . . . . ?
C6 C7 C8 N23 174.4(6) . . . . ?
C6 C7 N13 C14 119.8(7) . . . . ?
C9 C8 N23 C24 -61.2(9) . . . . ?
C10 O1 C2 C3 1.6(10) . . . . ?
C10 O1 C2 O11 -176.9(7) . . . . ?
C10 C5 C6 C7 -0.8(15) . . . . ?
C10 C9 C8 C7 3.4(15) . . . . ?
C10 C9 C8 N23 -176.3(8) . . . . ?
O11 C2 C3 C4 178.1(8) . . . . ?
C12 C4 C5 C6 -0.5(14) . . . . ?
C12 C4 C5 C10 178.4(8) . . . . ?
C7 C8 N23 C24 119.1(5) . . . . ?
C7 C8 C6A C5A -3(4) . . . . ?
C7 N13 C14 N15 169.1(4) . . . . ?
C7 N13 C14 O16 -12.0(6) . . . . ?
C7 C9A C10A O1A -180(2) . . . . ?
C7 C9A C10A C5A 3(4) . . . . ?
C8 C9 C10 O1 179.6(10) . . . . ?
C8 C9 C10 C5 0.0(17) . . . . ?
C8 C7 N13 C14 -61.2(5) . . . . ?
C8 C7 C9A C10A -4(3) . . . . ?
C8 N23 C24 N25 -163.4(4) . . . . ?
C8 N23 C24 O26 16.3(7) . . . . ?
N13 C7 C8 C9 175.8(8) . . . . ?
N13 C7 C8 N23 -4.6(5) . . . . ?
N13 C7 C8 C6A 179.8(18) . . . . ?
N13 C7 C9A C10A 180.0(19) . . . . ?
N13 C14 N15 C17 -176.7(4) . . . . ?
C14 N15 C17 C18 -159.2(4) . . . . ?
C14 N15 C17 C22 24.0(6) . . . . ?
N15 C17 C18 C19 -179.1(3) . . . . ?
N15 C17 C22 C21 179.7(3) . . . . ?
O16 C14 N15 C17 4.4(7) . . . . ?
C17 C18 C19 C20 0.2(6) . . . . ?
C18 C17 C22 C21 3.0(5) . . . . ?
C18 C19 C20 C21 1.1(5) . . . . ?
C19 C20 C21 C22 -0.3(5) . . . . ?
C20 C21 C22 C17 -1.7(5) . . . . ?
C22 C17 C18 C19 -2.2(5) . . . . ?
N23 C8 C6A C5A -179(2) . . . . ?
N23 C24 N25 C27 -176.8(4) . . . . ?
C24 N25 C27 C28 -149.5(4) . . . . ?
C24 N25 C27 C32 33.2(6) . . . . ?
N25 C27 C28 C29 -178.1(4) . . . . ?
N25 C27 C32 C31 178.3(4) . . . . ?
O26 C24 N25 C27 3.4(7) . . . . ?
C27 C28 C29 C30 -0.4(6) . . . . ?
C28 C27 C32 C31 1.1(6) . . . . ?
C28 C29 C30 C31 1.1(6) . . . . ?
C29 C30 C31 C32 -0.7(6) . . . . ?
C30 C31 C32 C27 -0.3(6) . . . . ?
C32 C27 C28 C29 -0.7(6) . . . . ?
O1A C2A C3A C4A -1(3) . . . . ?
C2A O1A C10A C5A 0(3) . . . . ?
C2A O1A C10A C9A -177(2) . . . . ?
C2A C3A C4A C5A 4(4) . . . . ?
C2A C3A C4A C12A 178.2(19) . . . . ?
C3A C4A C5A C6A 178(3) . . . . ?
C3A C4A C5A C10A -5(4) . . . . ?
C4A C5A C6A C8 180(3) . . . . ?
C4A C5A C10A O1A 4(4) . . . . ?
C4A C5A C10A C9A -180(3) . . . . ?
C6A C8 N23 C24 -66(2) . . . . ?
C6A C5A C10A O1A -180(3) . . . . ?
C6A C5A C10A C9A -3(4) . . . . ?
C9A C7 C8 N23 179.8(18) . . . . ?
C9A C7 C8 C6A 4(3) . . . . ?
C9A C7 N13 C14 115.1(16) . . . . ?
C10A O1A C2A C3A -1(3) . . . . ?
C10A O1A C2A O11A 176.3(19) . . . . ?
C10A C5A C6A C8 3(5) . . . . ?
O11A C2A C3A C4A -178(2) . . . . ?
C12A C4A C5A C6A 4(4) . . . . ?
C12A C4A C5A C10A -180(2) . . . . ?

loop_
_audit_author_email
mmet5356@chem.usyd.edu.au
?
philip.gale@sydney.edu.au
_olex2_date_sample_data_collection 2019-12-19
_olex2_date_sample_submission    2019-12-11
_olex2_exptl_crystal_mounting_method 'in paratone on a micromount'
_olex2_submission_original_sample_id HBisUreaCoumarine
_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 1.375
_oxdiff_exptl_absorpt_empirical_full_min 0.782
