# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_99536
_database_code_depnum_ccdc_archive 'CCDC 2240196'
loop_
_audit_author_name
_audit_author_address
'Patrick J Carroll'
;University of Pennsylvania
United States of America
;
_audit_update_record             
;
2024-01-04 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

#Crystallographer: Patrick J. Carroll

_audit_creation_date             2024-01-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2019/3
_chemical_formula_moiety         'C17 H15 F N2 O2, 0.125(H2 O)'
_chemical_formula_sum            'C17 H15.25 F N2 O2.125'
_chemical_formula_weight         300.56
_chemical_absolute_configuration .

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'
F F 0.0727 0.0534 '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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   29.9395(3)
_cell_length_b                   27.5788(3)
_cell_length_c                   7.07968(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5845.66(12)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    25458
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.3230
_cell_measurement_theta_min      2.9490
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.820
_exptl_absorpt_coefficient_mu    0.829
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             2516
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            35147
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.503
_diffrn_reflns_theta_min         4.359
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'HPC area detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix-6000HE
_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    -24.00  63.00   0.50    2.00    --   47.04 -59.00  90.00  174
  2  ω     31.00 120.00   0.50    2.00    --   47.04  59.00-128.00  178
  3  ω   -159.00 -70.00   0.50    8.00    --  -86.25 -59.00  90.00  178
  4  ω    -71.00 -14.00   0.50    8.00    --  -86.25  59.00-128.00  114
  5  ω     35.00  65.00   0.50    8.00    --  107.75 -59.00  90.00   60
  6  ω     92.00 178.00   0.50    8.00    --  107.75  59.00-128.00  172
  7  ω    -30.00  28.00   0.50    2.00    --  -47.04  19.00  30.00  116
  8  ω    -30.00  28.00   0.50    2.00    --  -47.04  19.00-180.00  116
  9  ω    -30.00  28.00   0.50    2.00    --  -47.04  19.00-120.00  116
 10  ω    -63.00  25.00   0.50    2.00    --  -47.04  59.00-128.00  176
 11  ω   -118.00 -31.00   0.50    2.00    --  -47.04 -59.00  90.00  174
 12  ω    -25.00  70.00   0.50    2.00    --   47.04 -77.00-180.00  190
 13  ω    -74.00 -13.00   0.50    8.00    --  -86.25  61.00  30.00  122
 14  ω    -38.00 -11.00   0.50    8.00    --  -86.25  30.00   0.00   54
 15  ω     35.00 132.00   0.50    8.00    --  107.75 -79.00  69.59  194
 16  ω     35.00  68.00   0.50    8.00    --  107.75 -61.00 -60.00   66
 17  ω     94.00 178.00   0.50    8.00    --  107.75  15.00 -90.00  168
 18  ω     35.00 103.00   0.50    8.00    --  107.75 -77.00   0.00  136
 19  ω     35.00 132.00   0.50    8.00    --  107.75 -80.00-142.39  194
 20  ω     91.00 178.00   0.50    8.00    --  107.75  61.00-180.00  174
 21  ω     35.00 132.00   0.50    8.00    --  107.75 -80.00 -72.43  194
 22  ω     35.00  68.00   0.50    8.00    --  107.75 -61.00   0.00   66
 23  ω     95.00 178.00   0.50    8.00    --  107.75  30.00   0.00  166
 24  ω     95.00 178.00   0.50    8.00    --  107.75  30.00 -60.00  166
 25  ω     35.00  68.00   0.50    8.00    --  107.75 -61.00  60.00   66
 26  ω     95.00 178.00   0.50    8.00    --  107.75  45.00 -90.00  166
 27  ω     35.00 132.00   0.50    8.00    --  107.75 -80.00  27.20  194
 28  ω     35.00  68.00   0.50    8.00    --  107.75 -61.00 150.00   66
 29  ω     95.00 178.00   0.50    8.00    --  107.75  45.00  60.00  166
 30  ω     35.00 103.00   0.50    8.00    --  107.75 -77.00 -90.00  136
 31  ω     85.00 178.00   0.50    8.00    --  107.75  77.00 120.00  186
 32  ω     35.00 103.00   0.50    8.00    --  107.75 -77.00-180.00  136
 33  ω     35.00 103.00   0.50    8.00    --  107.75 -77.00 150.00  136
 34  ω     35.00  68.00   0.50    8.00    --  107.75 -61.00-150.00   66
 35  ω     95.00 178.00   0.50    8.00    --  107.75  30.00  60.00  166
 36  ω     35.00 132.00   0.50    8.00    --  107.75 -80.00 120.93  194
 37  ω     35.00 103.00   0.50    8.00    --  107.75 -77.00 -60.00  136
 38  ω     35.00 103.00   0.50    8.00    --  107.75 -77.00 -30.00  136
 39  ω     35.00 103.00   0.50    8.00    --  107.75 -77.00  30.00  136
 40  ω     35.00 132.00   0.50    8.00    --  107.75 -80.00-100.39  194
 41  ω     35.00 132.00   0.50    8.00    --  107.75 -80.00 151.11  194
 42  ω     35.00 132.00   0.50    8.00    --  107.75 -79.00-159.50  194
 43  ω     95.00 178.00   0.50    8.00    --  107.75  45.00 150.00  166
 44  ω   -119.00 -24.00   0.50    2.00    --  -47.04 -77.00   0.00  190
 45  ω   -118.00 -32.00   0.50    2.00    --  -47.04 -57.00 -90.00  172
 46  ω   -119.00 -24.00   0.50    2.00    --  -47.04 -77.00  60.00  190
 47  ω     24.00 120.00   0.50    2.00    --   47.04  77.00 150.00  192
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0339910000
_diffrn_orient_matrix_UB_12      -0.0416122000
_diffrn_orient_matrix_UB_13      0.0208038000
_diffrn_orient_matrix_UB_21      0.0117558000
_diffrn_orient_matrix_UB_22      -0.0045253000
_diffrn_orient_matrix_UB_23      0.2111295000
_diffrn_orient_matrix_UB_31      -0.0367973000
_diffrn_orient_matrix_UB_32      0.0369825000
_diffrn_orient_matrix_UB_33      0.0485163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2938
_reflns_number_total             2976
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 1321 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+4.6832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0982
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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,H) groups
2. Others
 Fixed Sof: O18(0.125) H18A(0.125) H18B(0.125)
 Fixed X: H18A(0.51765) H18B(0.480539)
 Fixed Y: H18A(0.48566) H18B(0.51494)
 Fixed Z: H18A(1.10291) H18B(1.09311)
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual

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
C1 C 0.67861(7) 0.64779(8) 0.4534(4) 0.0358(5) Uani 1 1 d . . . . .
C2 C 0.71618(7) 0.61481(8) 0.4363(3) 0.0353(5) Uani 1 1 d . . . . .
C3 C 0.70176(7) 0.56830(9) 0.4697(3) 0.0351(5) Uani 1 1 d . . . . .
C4 C 0.62079(8) 0.54111(8) 0.5565(3) 0.0336(5) Uani 1 1 d . . . . .
C5 C 0.58388(7) 0.57002(8) 0.5737(4) 0.0354(5) Uani 1 1 d . . . . .
C6 C 0.59638(7) 0.61995(8) 0.5385(3) 0.0319(4) Uani 1 1 d . . . . .
C7 C 0.53762(9) 0.55528(10) 0.6239(6) 0.0578(8) Uani 1 1 d . . . . .
H7A H 0.521313 0.546477 0.508818 0.087 Uiso 1 1 calc R U . . .
H7B H 0.522396 0.582309 0.686558 0.087 Uiso 1 1 calc R U . . .
H7C H 0.538637 0.527332 0.709238 0.087 Uiso 1 1 calc R U . . .
C8 C 0.62555(8) 0.48799(8) 0.5823(4) 0.0416(6) Uani 1 1 d . . . . .
H8A H 0.630290 0.472556 0.459250 0.062 Uiso 1 1 calc R U . . .
H8B H 0.598344 0.474979 0.640235 0.062 Uiso 1 1 calc R U . . .
H8C H 0.651163 0.481337 0.664519 0.062 Uiso 1 1 calc R U . . .
C9 C 0.76096(8) 0.63237(11) 0.3751(5) 0.0486(6) Uani 1 1 d . . . . .
H9A H 0.757845 0.664027 0.313581 0.073 Uiso 1 1 calc R U . . .
H9B H 0.773993 0.609168 0.285931 0.073 Uiso 1 1 calc R U . . .
H9C H 0.780494 0.635484 0.485510 0.073 Uiso 1 1 calc R U . . .
C10 C 0.72592(7) 0.52276(9) 0.4654(3) 0.0368(5) Uani 1 1 d . . . . .
H10 H 0.710392 0.493701 0.435747 0.044 Uiso 1 1 calc R U . . .
C11 C 0.76998(7) 0.52092(9) 0.5027(3) 0.0361(5) Uani 1 1 d . . . . .
H11 H 0.783903 0.550819 0.533956 0.043 Uiso 1 1 calc R U . . .
C12 C 0.79887(7) 0.47812(8) 0.5006(3) 0.0345(5) Uani 1 1 d . . . . .
C13 C 0.78439(7) 0.43154(9) 0.4495(3) 0.0359(5) Uani 1 1 d . . . . .
H13 H 0.754289 0.426568 0.411761 0.043 Uiso 1 1 calc R U . . .
C14 C 0.81386(8) 0.39270(9) 0.4540(4) 0.0391(5) Uani 1 1 d . . . . .
H14 H 0.804272 0.361050 0.419968 0.047 Uiso 1 1 calc R U . . .
C15 C 0.85742(8) 0.40110(9) 0.5089(4) 0.0384(5) Uani 1 1 d . . . . .
C16 C 0.87313(8) 0.44607(9) 0.5582(4) 0.0398(5) Uani 1 1 d . . . . .
H16 H 0.903400 0.450714 0.594133 0.048 Uiso 1 1 calc R U . . .
C17 C 0.84321(8) 0.48467(9) 0.5537(3) 0.0373(5) Uani 1 1 d . . . . .
H17 H 0.853269 0.516161 0.587623 0.045 Uiso 1 1 calc R U . . .
N1 N 0.65631(7) 0.56996(7) 0.5070(4) 0.0411(5) Uani 1 1 d . . . . .
N2 N 0.64203(6) 0.61730(7) 0.4984(4) 0.0410(5) Uani 1 1 d . . . . .
O1 O 0.67590(6) 0.69171(6) 0.4347(3) 0.0442(4) Uani 1 1 d . . . . .
O2 O 0.57457(5) 0.65726(6) 0.5415(3) 0.0374(4) Uani 1 1 d . . . . .
F1 F 0.88603(5) 0.36294(6) 0.5133(3) 0.0536(4) Uani 1 1 d . . . . .
O18 O 0.500000 0.500000 1.0229(17) 0.053(3) Uani 0.25 2 d S T P . .
H18A H 0.517650 0.485660 1.102909 0.079 Uiso 0.125 1 d . U P . .
H18B H 0.480539 0.514940 1.093109 0.079 Uiso 0.125 1 d . U P . .


_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
C1 C2 1.452(3) . ?
C1 N2 1.417(3) . ?
C1 O1 1.221(3) . ?
C2 C3 1.374(3) . ?
C2 C9 1.490(3) . ?
C3 C10 1.450(3) . ?
C3 N1 1.387(3) . ?
C4 C5 1.368(3) . ?
C4 C8 1.483(3) . ?
C4 N1 1.374(3) . ?
C5 C6 1.448(3) . ?
C5 C7 1.487(3) . ?
C6 N2 1.398(3) . ?
C6 O2 1.219(3) . ?
C10 C11 1.346(3) . ?
C11 C12 1.464(3) . ?
C12 C13 1.403(3) . ?
C12 C17 1.392(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.371(3) . ?
C15 F1 1.357(3) . ?
C16 C17 1.392(3) . ?
N1 N2 1.375(3) . ?

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
N2 C1 C2 104.22(18) . . ?
O1 C1 C2 131.6(2) . . ?
O1 C1 N2 124.2(2) . . ?
C1 C2 C9 121.2(2) . . ?
C3 C2 C1 109.11(19) . . ?
C3 C2 C9 129.5(2) . . ?
C2 C3 C10 130.4(2) . . ?
C2 C3 N1 108.07(19) . . ?
N1 C3 C10 121.5(2) . . ?
C5 C4 C8 130.0(2) . . ?
C5 C4 N1 108.1(2) . . ?
N1 C4 C8 122.0(2) . . ?
C4 C5 C6 109.28(19) . . ?
C4 C5 C7 127.9(2) . . ?
C6 C5 C7 122.8(2) . . ?
N2 C6 C5 103.76(18) . . ?
O2 C6 C5 131.4(2) . . ?
O2 C6 N2 124.86(19) . . ?
C11 C10 C3 121.2(2) . . ?
C10 C11 C12 127.4(2) . . ?
C13 C12 C11 123.9(2) . . ?
C17 C12 C11 117.1(2) . . ?
C17 C12 C13 118.9(2) . . ?
C14 C13 C12 120.3(2) . . ?
C15 C14 C13 118.5(2) . . ?
C16 C15 C14 123.2(2) . . ?
F1 C15 C14 118.2(2) . . ?
F1 C15 C16 118.6(2) . . ?
C15 C16 C17 117.7(2) . . ?
C12 C17 C16 121.4(2) . . ?
C4 N1 C3 142.1(2) . . ?
C4 N1 N2 108.70(18) . . ?
N2 N1 C3 109.15(18) . . ?
C6 N2 C1 140.38(18) . . ?
N1 N2 C1 109.45(18) . . ?
N1 N2 C6 110.16(17) . . ?

_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 1.938
_oxdiff_exptl_absorpt_empirical_full_min 0.505
####################################################################### 
# 
# 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_99534
_database_code_depnum_ccdc_archive 'CCDC 2240197'
loop_
_audit_author_name
_audit_author_address
'Patrick J Carroll'
;University of Pennsylvania
United States of America
;
_audit_update_record             
;
2024-01-04 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

# Crystallographer: Patrick J. Carroll

_audit_creation_date             2021-06-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C17 H15 N3 O4'
_chemical_formula_sum            'C17 H15 N3 O4'
_chemical_formula_weight         325.32
_chemical_absolute_configuration .

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.85501(8)
_cell_length_b                   13.3190(3)
_cell_length_c                   14.7962(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.880(2)
_cell_angle_gamma                90
_cell_volume                     756.96(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15383
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      3.0450
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       bar
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19219
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.341
_diffrn_reflns_theta_min         2.061
_diffrn_ambient_temperature      100
_diffrn_detector                 'HPC area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            HyPix-6000HE
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  63.00   0.50    5.00    --   -9.90  57.00 -93.00  176
  2  ω    -81.00   5.00   0.50    5.00    --   -9.90 -57.00 124.00  172
  3  ω     -4.00  81.00   0.50    5.00    --    8.18  37.00  60.00  170
  4  ω    -65.00  18.00   0.50    5.00    --    8.18 -37.00-120.00  166
  5  ω     -4.00  84.00   0.50    5.00    --    8.18  19.00 -90.00  176
  6  ω    -14.00  81.00   0.50    5.00    --    8.18  77.00  60.00  190
  7  ω    -83.00   3.00   0.50    5.00    --   -9.90 -37.00 120.00  172
  8  ω    -81.00   5.00   0.50    5.00    --   -9.90 -57.00 -90.00  172
  9  ω    -83.00   3.00   0.50    5.00    --   -9.90 -37.00 -60.00  172
 10  ω    -67.00   2.00   0.50    5.00    --    8.18 -19.00  60.00  138
 11  ω    -25.00  45.00   0.50    5.00    --   -9.90  57.00 120.00  140
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0120041000
_diffrn_orient_matrix_UB_12      -0.0403593000
_diffrn_orient_matrix_UB_13      0.0314091000
_diffrn_orient_matrix_UB_21      0.1813787000
_diffrn_orient_matrix_UB_22      0.0087504000
_diffrn_orient_matrix_UB_23      0.0084948000
_diffrn_orient_matrix_UB_31      -0.0327347000
_diffrn_orient_matrix_UB_32      0.0336106000
_diffrn_orient_matrix_UB_33      0.0354409000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2734
_reflns_number_total             2782
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1295 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2782
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0237
_refine_ls_restrained_S_all      1.029
_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)+(0.0390P)²+0.1383P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0629
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual

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
C1 C 0.1234(5) 0.81947(14) 0.62857(12) 0.0149(4) Uani 1 1 d . . . . .
C2 C 0.3136(5) 0.77483(14) 0.70782(13) 0.0151(4) Uani 1 1 d . . . . .
C3 C 0.3574(5) 0.67523(14) 0.69175(12) 0.0137(4) Uani 1 1 d . . . . .
C4 C 0.3484(4) 0.59733(14) 0.53235(12) 0.0140(4) Uani 1 1 d . . . . .
C5 C 0.2687(5) 0.64582(13) 0.45289(12) 0.0147(4) Uani 1 1 d . . . . .
C6 C 0.0930(5) 0.73916(14) 0.47035(12) 0.0147(4) Uani 1 1 d . . . . .
C7 C 0.3465(5) 0.61579(14) 0.35954(13) 0.0174(4) Uani 1 1 d . . . . .
H7a H 0.130186 0.596097 0.324426 0.026 Uiso 1 1 calc GR . . . .
H7b H 0.508840 0.559027 0.363190 0.026 Uiso 1 1 calc GR . . . .
H7c H 0.451572 0.672534 0.329712 0.026 Uiso 1 1 calc GR . . . .
C8 C 0.5307(5) 0.49976(13) 0.54683(13) 0.0157(4) Uani 1 1 d . . . . .
H8a H 0.697065 0.504210 0.600580 0.024 Uiso 1 1 calc GR . . . .
H8b H 0.655345 0.483723 0.493632 0.024 Uiso 1 1 calc GR . . . .
H8c H 0.360116 0.446932 0.555847 0.024 Uiso 1 1 calc GR . . . .
C9 C 0.4135(5) 0.83495(14) 0.79100(13) 0.0192(4) Uani 1 1 d . . . . .
H9a H 0.202903 0.858440 0.817185 0.029 Uiso 1 1 calc GR . . . .
H9b H 0.552982 0.892851 0.775148 0.029 Uiso 1 1 calc GR . . . .
H9c H 0.550173 0.793078 0.835347 0.029 Uiso 1 1 calc GR . . . .
C10 C 0.4858(5) 0.59890(14) 0.75631(12) 0.0146(4) Uani 1 1 d . . . . .
H10 H 0.655490 0.618019 0.803489 0.018 Uiso 1 1 calc R . . . .
C11 C 0.3785(5) 0.50274(14) 0.75325(12) 0.0148(4) Uani 1 1 d . . . . .
H11 H 0.212537 0.484742 0.704817 0.018 Uiso 1 1 calc R . . . .
C12 C 0.4924(5) 0.42315(14) 0.81721(12) 0.0141(4) Uani 1 1 d . . . . .
C13 C 0.3930(5) 0.32414(14) 0.79484(12) 0.0163(4) Uani 1 1 d . . . . .
H13 H 0.253217 0.311406 0.740030 0.020 Uiso 1 1 calc R . . . .
C14 C 0.4956(5) 0.24488(14) 0.85140(13) 0.0168(4) Uani 1 1 d . . . . .
H14 H 0.428186 0.177979 0.836143 0.020 Uiso 1 1 calc R . . . .
C15 C 0.6997(5) 0.26575(14) 0.93101(13) 0.0169(4) Uani 1 1 d . . . . .
C16 C 0.8010(5) 0.36259(15) 0.95587(12) 0.0165(4) Uani 1 1 d . . . . .
H16 H 0.939120 0.374706 1.011062 0.020 Uiso 1 1 calc R . . . .
C17 C 0.6970(5) 0.44098(14) 0.89871(12) 0.0155(4) Uani 1 1 d . . . . .
H17 H 0.764595 0.507665 0.914733 0.019 Uiso 1 1 calc R . . . .
N1 N 0.2083(4) 0.65072(11) 0.60372(10) 0.0135(3) Uani 1 1 d . . . . .
N2 N 0.0616(4) 0.73914(11) 0.56630(10) 0.0143(3) Uani 1 1 d . . . . .
N3 N 0.8205(4) 0.18149(12) 0.98950(11) 0.0199(4) Uani 1 1 d . . . . .
O1 O 0.0200(4) 0.90495(10) 0.61551(9) 0.0188(3) Uani 1 1 d . . . . .
O2 O -0.0158(3) 0.80578(10) 0.41974(9) 0.0185(3) Uani 1 1 d . . . . .
O3 O 1.0166(4) 0.19968(12) 1.05746(10) 0.0293(4) Uani 1 1 d . . . . .
O4 O 0.7250(5) 0.09639(11) 0.96750(11) 0.0351(4) Uani 1 1 d . . . . .


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
C1 C2 1.456(3) . ?
C1 N2 1.419(2) . ?
C1 O1 1.216(2) . ?
C2 C3 1.361(3) . ?
C2 C9 1.491(3) . ?
C3 C10 1.453(2) . ?
C3 N1 1.416(2) . ?
C4 C5 1.354(3) . ?
C4 C8 1.484(2) . ?
C4 N1 1.418(2) . ?
C5 C6 1.450(3) . ?
C5 C7 1.493(3) . ?
C6 N2 1.435(2) . ?
C6 O2 1.213(2) . ?
C10 C11 1.345(3) . ?
C11 C12 1.463(2) . ?
C12 C13 1.405(3) . ?
C12 C17 1.404(3) . ?
C13 C14 1.384(3) . ?
C14 C15 1.388(3) . ?
C15 C16 1.388(3) . ?
C15 N3 1.469(2) . ?
C16 C17 1.381(3) . ?
N1 N2 1.400(2) . ?
N3 O3 1.230(2) . ?
N3 O4 1.227(2) . ?

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
N2 C1 C2 105.09(15) . . ?
O1 C1 C2 130.24(18) . . ?
O1 C1 N2 124.61(17) . . ?
C1 C2 C9 121.50(16) . . ?
C3 C2 C1 108.59(17) . . ?
C3 C2 C9 129.84(18) . . ?
C2 C3 C10 127.42(17) . . ?
C2 C3 N1 109.79(16) . . ?
N1 C3 C10 122.17(16) . . ?
C5 C4 C8 127.80(17) . . ?
C5 C4 N1 109.57(16) . . ?
N1 C4 C8 122.51(16) . . ?
C4 C5 C6 109.23(16) . . ?
C4 C5 C7 128.84(17) . . ?
C6 C5 C7 121.91(16) . . ?
N2 C6 C5 104.84(15) . . ?
O2 C6 C5 131.29(17) . . ?
O2 C6 N2 123.87(17) . . ?
C11 C10 C3 123.89(16) . . ?
C10 C11 C12 126.40(17) . . ?
C13 C12 C11 117.83(16) . . ?
C17 C12 C11 123.28(17) . . ?
C17 C12 C13 118.89(17) . . ?
C14 C13 C12 121.02(17) . . ?
C13 C14 C15 118.21(17) . . ?
C14 C15 C16 122.51(17) . . ?
C14 C15 N3 118.40(17) . . ?
C16 C15 N3 119.07(16) . . ?
C17 C16 C15 118.66(17) . . ?
C16 C17 C12 120.70(17) . . ?
C3 N1 C4 130.54(15) . . ?
N2 N1 C3 106.78(14) . . ?
N2 N1 C4 107.10(14) . . ?
C1 N2 C6 128.21(15) . . ?
N1 N2 C1 109.73(13) . . ?
N1 N2 C6 109.04(14) . . ?
O3 N3 C15 118.26(17) . . ?
O4 N3 C15 118.47(16) . . ?
O4 N3 O3 123.26(17) . . ?

_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 1.384
_oxdiff_exptl_absorpt_empirical_full_min 0.728
####################################################################### 
# 
# 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_99590
_database_code_depnum_ccdc_archive 'CCDC 2240198'
loop_
_audit_author_name
_audit_author_address
' Patrick J Carroll'
;University of Pennsylvania
United States of America
;
_audit_update_record             
;
2023-02-06 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

#Crystallographer: Michael R. Gau

_audit_creation_date             2022-03-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C19 H21 N3 O2, C H4 O'
_chemical_formula_sum            'C20 H25 N3 O3'
_chemical_formula_weight         355.43

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.0514(6)
_cell_length_b                   17.1123(10)
_cell_length_c                   30.720(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.352(8)
_cell_angle_gamma                90
_cell_volume                     3705.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15223
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.0610
_cell_measurement_theta_min      2.6310
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            'red orange'
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       plate
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.04
_diffrn_reflns_av_R_equivalents  0.081
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            49137
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.475
_diffrn_reflns_theta_min         2.318
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'HPC area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'Dectris Pilatus3 R 200K'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  85.00   0.50   60.00    --   17.64  19.00  60.00  264
  2  ω     27.00  59.00   0.50   60.00    --   17.64  57.00  60.00   64
  3  ω    -22.00   3.00   0.50   60.00    --   17.64  77.00 150.00   50
  4  ω    -19.00  45.00   0.50   60.00    --   17.64  57.00  30.00  128
  5  ω    -19.00   7.00   0.50   60.00    --   17.64 -77.00-150.00   52
  6  ω    -25.00  36.00   0.50   60.00    --   17.64 -77.00-120.00  122
  7  ω     -1.00  54.00   0.50   60.00    --   17.64  57.00-150.00  110
  8  ω    -18.00  16.00   0.50   60.00    --   17.64  57.00  90.00   68
  9  ω    -72.00 -46.00   0.50   60.00    --   17.64 -19.00  60.00   52
 10  ω    -44.00   3.00   0.50   60.00    --   17.64 -19.00  60.00   94
 11  ω     -1.00  25.00   0.50   60.00    --   17.64  77.00 -60.00   52
 12  ω    -21.00  21.00   0.50   60.00    --  -17.95 -77.00  90.00   84
 13  ω    -42.00  24.00   0.50   60.00    --  -17.95  77.00  90.00  132
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0004409000
_diffrn_orient_matrix_UB_12      0.0031152000
_diffrn_orient_matrix_UB_13      -0.0230201000
_diffrn_orient_matrix_UB_21      0.0963347000
_diffrn_orient_matrix_UB_22      -0.0119162000
_diffrn_orient_matrix_UB_23      -0.0000139000
_diffrn_orient_matrix_UB_31      -0.0289598000
_diffrn_orient_matrix_UB_32      -0.0395975000
_diffrn_orient_matrix_UB_33      -0.0017878000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_number_gt                9577
_reflns_number_total             13556
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     484
_refine_ls_number_reflns         13556
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0719
_refine_ls_restrained_S_all      1.047
_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)+(0.1260P)²+0.9687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1949
_refine_ls_wR_factor_ref         0.2144
_refine_special_details          
;
 Refined as a 2-component twin.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual

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 0.9004(5) 0.54496(16) 0.67429(7) 0.0386(7) Uani 1 1 d . . . . .
O2 O 0.8088(5) 0.45934(15) 0.58237(8) 0.0403(7) Uani 1 1 d . . . . .
N1 N 0.8291(5) 0.58940(17) 0.60428(8) 0.0281(7) Uani 1 1 d . . . . .
N2 N 0.8327(5) 0.66012(16) 0.58351(8) 0.0237(6) Uani 1 1 d . . . . .
N3 N 0.9437(5) 0.94132(19) 0.33973(9) 0.0332(8) Uani 1 1 d . . . . .
C1 C 0.8878(6) 0.5996(2) 0.64808(10) 0.0286(8) Uani 1 1 d . . . . .
C2 C 0.9227(5) 0.6816(2) 0.65234(10) 0.0259(8) Uani 1 1 d . . . . .
C3 C 0.8957(5) 0.71664(19) 0.61306(9) 0.0207(7) Uani 1 1 d . . . . .
C4 C 0.9800(6) 0.7204(2) 0.69479(10) 0.0351(9) Uani 1 1 d . . . . .
H4a H 1.111019 0.739139 0.693170 0.053 Uiso 1 1 calc R U . . .
H4b H 0.970664 0.682669 0.718621 0.053 Uiso 1 1 calc R U . . .
H4c H 0.895547 0.764724 0.700119 0.053 Uiso 1 1 calc R U . . .
C5 C 0.9143(6) 0.7995(2) 0.60035(10) 0.0256(8) Uani 1 1 d . . . . .
H5a H 1.000230 0.803647 0.575851 0.038 Uiso 1 1 calc R U . . .
H5b H 0.965549 0.829596 0.625075 0.038 Uiso 1 1 calc R U . . .
H5c H 0.789380 0.820139 0.591690 0.038 Uiso 1 1 calc R U . . .
C6 C 0.8115(6) 0.5285(2) 0.57299(11) 0.0282(8) Uani 1 1 d . . . . .
C7 C 0.8001(5) 0.5686(2) 0.53190(10) 0.0246(8) Uani 1 1 d . . . . .
C8 C 0.8217(5) 0.6469(2) 0.53873(9) 0.0199(7) Uani 1 1 d . . . . .
C9 C 0.7542(6) 0.5264(2) 0.48988(10) 0.0313(8) Uani 1 1 d . . . . .
H9a H 0.673523 0.559654 0.471203 0.047 Uiso 1 1 calc R U . . .
H9b H 0.687123 0.477698 0.496174 0.047 Uiso 1 1 calc R U . . .
H9c H 0.871968 0.514486 0.474934 0.047 Uiso 1 1 calc R U . . .
C10 C 0.8248(5) 0.71158(19) 0.50849(9) 0.0189(7) Uani 1 1 d . . . . .
H10 H 0.780709 0.761153 0.517801 0.023 Uiso 1 1 calc R U . . .
C11 C 0.8874(5) 0.7044(2) 0.46788(9) 0.0207(7) Uani 1 1 d . . . . .
H11 H 0.929945 0.654051 0.459461 0.025 Uiso 1 1 calc R U . . .
C12 C 0.8968(5) 0.76593(19) 0.43539(9) 0.0191(7) Uani 1 1 d . . . . .
C13 C 0.8464(5) 0.8432(2) 0.44313(9) 0.0229(7) Uani 1 1 d . . . . .
H13 H 0.800570 0.856858 0.470945 0.028 Uiso 1 1 calc R U . . .
C14 C 0.8606(5) 0.9007(2) 0.41198(10) 0.0246(7) Uani 1 1 d . . . . .
H14 H 0.826052 0.952849 0.418907 0.030 Uiso 1 1 calc R U . . .
C15 C 0.9249(5) 0.8836(2) 0.37036(10) 0.0256(8) Uani 1 1 d . . . . .
C16 C 0.9748(5) 0.8051(2) 0.36190(10) 0.0264(8) Uani 1 1 d . . . . .
H16 H 1.018747 0.791184 0.333957 0.032 Uiso 1 1 calc R U . . .
C17 C 0.9606(5) 0.7485(2) 0.39364(9) 0.0239(7) Uani 1 1 d . . . . .
H17 H 0.995146 0.696286 0.386998 0.029 Uiso 1 1 calc R U . . .
C18 C 0.8802(7) 1.0195(2) 0.34844(12) 0.0397(10) Uani 1 1 d . . . . .
H18d H 0.741730 1.019835 0.350560 0.060 Uiso 1 1 calc R U . . .
H18e H 0.917810 1.054105 0.324740 0.060 Uiso 1 1 calc R U . . .
H18f H 0.937704 1.037789 0.375940 0.060 Uiso 1 1 calc R U . . .
C19 C 0.9814(7) 0.9210(3) 0.29476(11) 0.0395(10) Uani 1 1 d . . . . .
H19d H 1.089241 0.885011 0.293954 0.059 Uiso 1 1 calc R U . . .
H19e H 1.011102 0.968546 0.278465 0.059 Uiso 1 1 calc R U . . .
H19f H 0.869103 0.895914 0.281578 0.059 Uiso 1 1 calc R U . . .
O1' O 0.5227(4) 0.07251(15) 0.68577(7) 0.0340(7) Uani 1 1 d . . . . .
O2' O 0.6467(4) -0.03303(14) 0.60346(8) 0.0342(6) Uani 1 1 d . . . . .
N1' N 0.6046(5) 0.10003(16) 0.61472(8) 0.0242(6) Uani 1 1 d . . . . .
N2' N 0.6082(4) 0.16568(15) 0.58922(8) 0.0216(6) Uani 1 1 d . . . . .
N3' N 0.5863(6) 0.4103(2) 0.33424(8) 0.0365(8) Uani 1 1 d . . . . .
C1' C 0.5423(5) 0.1192(2) 0.65645(10) 0.0251(8) Uani 1 1 d . . . . .
C2' C 0.5138(5) 0.2036(2) 0.65437(10) 0.0244(7) Uani 1 1 d . . . . .
C3' C 0.5511(5) 0.22885(19) 0.61388(9) 0.0205(7) Uani 1 1 d . . . . .
C4' C 0.4540(6) 0.2506(2) 0.69252(10) 0.0354(9) Uani 1 1 d . . . . .
H4'c H 0.564199 0.260585 0.711758 0.053 Uiso 1 1 calc R U . . .
H4'a H 0.357962 0.221688 0.708499 0.053 Uiso 1 1 calc R U . . .
H4'b H 0.400598 0.300425 0.682378 0.053 Uiso 1 1 calc R U . . .
C5' C 0.5430(5) 0.30929(19) 0.59609(10) 0.0238(7) Uani 1 1 d . . . . .
H5'a H 0.671727 0.327334 0.590160 0.036 Uiso 1 1 calc R U . . .
H5'b H 0.485232 0.344172 0.617335 0.036 Uiso 1 1 calc R U . . .
H5'c H 0.466634 0.309583 0.569022 0.036 Uiso 1 1 calc R U . . .
C6' C 0.6421(5) 0.0340(2) 0.58937(10) 0.0263(8) Uani 1 1 d . . . . .
C7' C 0.6735(5) 0.0650(2) 0.54639(10) 0.0257(8) Uani 1 1 d . . . . .
C8' C 0.6486(5) 0.1445(2) 0.54715(9) 0.0207(7) Uani 1 1 d . . . . .
C9' C 0.7497(6) 0.0150(2) 0.51115(11) 0.0337(9) Uani 1 1 d . . . . .
H9'a H 0.644819 -0.003369 0.492303 0.051 Uiso 1 1 calc R U . . .
H9'b H 0.815867 -0.030045 0.524089 0.051 Uiso 1 1 calc R U . . .
H9'c H 0.838462 0.045431 0.493892 0.051 Uiso 1 1 calc R U . . .
C10' C 0.6602(5) 0.2029(2) 0.51339(9) 0.0229(7) Uani 1 1 d . . . . .
H10' H 0.692379 0.254780 0.521786 0.028 Uiso 1 1 calc R U . . .
C11' C 0.6283(5) 0.1885(2) 0.47076(9) 0.0218(7) Uani 1 1 d . . . . .
H11' H 0.603435 0.135825 0.462697 0.026 Uiso 1 1 calc R U . . .
C12' C 0.6283(5) 0.2459(2) 0.43594(9) 0.0226(7) Uani 1 1 d . . . . .
C13' C 0.6718(5) 0.3248(2) 0.44251(9) 0.0230(7) Uani 1 1 d . . . . .
H13' H 0.710121 0.341793 0.470813 0.028 Uiso 1 1 calc R U . . .
C14' C 0.6608(5) 0.3782(2) 0.40947(10) 0.0258(8) Uani 1 1 d . . . . .
H14' H 0.693058 0.431209 0.415245 0.031 Uiso 1 1 calc R U . . .
C15' C 0.6022(5) 0.3561(2) 0.36661(9) 0.0256(8) Uani 1 1 d . . . . .
C16' C 0.5645(5) 0.2761(2) 0.35978(10) 0.0257(8) Uani 1 1 d . . . . .
H16' H 0.530413 0.258287 0.331367 0.031 Uiso 1 1 calc R U . . .
C17' C 0.5763(5) 0.2236(2) 0.39336(9) 0.0244(7) Uani 1 1 d . . . . .
H17' H 0.548326 0.170225 0.387632 0.029 Uiso 1 1 calc R U . . .
C18' C 0.6088(7) 0.4926(2) 0.34345(11) 0.0400(10) Uani 1 1 d . . . . .
H18a H 0.525419 0.507431 0.367134 0.060 Uiso 1 1 calc R U . . .
H18b H 0.575396 0.522923 0.317325 0.060 Uiso 1 1 calc R U . . .
H18c H 0.740967 0.503182 0.352124 0.060 Uiso 1 1 calc R U . . .
C19' C 0.5355(7) 0.3879(3) 0.28966(10) 0.0410(11) Uani 1 1 d . . . . .
H19a H 0.626421 0.349170 0.279328 0.062 Uiso 1 1 calc R U . . .
H19b H 0.538091 0.434121 0.270870 0.062 Uiso 1 1 calc R U . . .
H19c H 0.407714 0.365293 0.288839 0.062 Uiso 1 1 calc R U . . .
O3 O 0.8344(5) 0.37768(16) 0.67545(8) 0.0469(9) Uani 1 1 d . . . . .
H3 H 0.854333 0.421051 0.663595 0.070 Uiso 1 1 calc R U . . .
C20 C 0.9124(8) 0.3780(3) 0.71792(13) 0.0536(13) Uani 1 1 d . . . . .
H20a H 1.042208 0.398441 0.717443 0.080 Uiso 1 1 calc R U . . .
H20b H 0.914244 0.324632 0.729444 0.080 Uiso 1 1 calc R U . . .
H20c H 0.835259 0.411271 0.736509 0.080 Uiso 1 1 calc R U . . .
O3' O 0.7110(5) -0.10715(19) 0.68513(9) 0.0524(9) Uani 1 1 d . . . . .
H3' H 0.668521 -0.081417 0.663755 0.079 Uiso 1 1 calc R U . . .
C20' C 0.5857(9) -0.1030(3) 0.71854(13) 0.0513(13) Uani 1 1 d . . . . .
H20e H 0.581245 -0.049295 0.729543 0.077 Uiso 1 1 calc R U . . .
H20f H 0.627275 -0.138186 0.742059 0.077 Uiso 1 1 calc R U . . .
H20d H 0.459215 -0.118555 0.707877 0.077 Uiso 1 1 calc R U . . .


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 C1 1.235(4) . ?
O2 C6 1.219(4) . ?
N1 N2 1.369(4) . ?
N1 C1 1.409(4) . ?
N1 C6 1.421(4) . ?
N2 C3 1.392(4) . ?
N2 C8 1.394(4) . ?
N3 C15 1.373(4) . ?
N3 C18 1.438(5) . ?
N3 C19 1.455(5) . ?
C1 C2 1.430(5) . ?
C2 C3 1.357(4) . ?
C2 C4 1.510(5) . ?
C3 C5 1.477(5) . ?
C6 C7 1.437(5) . ?
C7 C8 1.364(5) . ?
C7 C9 1.508(4) . ?
C8 C10 1.445(4) . ?
C10 C11 1.339(4) . ?
C11 C12 1.453(4) . ?
C12 C13 1.391(5) . ?
C12 C17 1.401(4) . ?
C13 C14 1.378(5) . ?
C14 C15 1.398(5) . ?
C15 C16 1.414(5) . ?
C16 C17 1.380(5) . ?
O1' C1' 1.215(4) . ?
O2' C6' 1.225(4) . ?
N1' N2' 1.370(4) . ?
N1' C1' 1.404(4) . ?
N1' C6' 1.401(4) . ?
N2' C3' 1.385(4) . ?
N2' C8' 1.378(4) . ?
N3' C15' 1.362(5) . ?
N3' C18' 1.445(5) . ?
N3' C19' 1.459(4) . ?
C1' C2' 1.459(5) . ?
C2' C3' 1.348(4) . ?
C2' C4' 1.490(5) . ?
C3' C5' 1.482(4) . ?
C6' C7' 1.445(5) . ?
C7' C8' 1.373(5) . ?
C7' C9' 1.490(5) . ?
C8' C10' 1.444(5) . ?
C10' C11' 1.347(4) . ?
C11' C12' 1.452(5) . ?
C12' C13' 1.398(5) . ?
C12' C17' 1.403(4) . ?
C13' C14' 1.367(5) . ?
C14' C15' 1.422(4) . ?
C15' C16' 1.409(5) . ?
C16' C17' 1.369(5) . ?
O3 C20 1.404(5) . ?
O3' C20' 1.372(5) . ?

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
N2 N1 C1 109.1(3) . . ?
N2 N1 C6 109.6(2) . . ?
C1 N1 C6 139.1(3) . . ?
N1 N2 C3 108.6(2) . . ?
N1 N2 C8 108.4(3) . . ?
C3 N2 C8 140.0(3) . . ?
C15 N3 C18 120.4(3) . . ?
C15 N3 C19 120.1(3) . . ?
C18 N3 C19 117.6(3) . . ?
O1 C1 N1 122.9(3) . . ?
O1 C1 C2 132.3(3) . . ?
N1 C1 C2 104.8(3) . . ?
C1 C2 C4 123.6(3) . . ?
C3 C2 C1 109.4(3) . . ?
C3 C2 C4 127.0(3) . . ?
N2 C3 C5 121.6(3) . . ?
C2 C3 N2 108.0(3) . . ?
C2 C3 C5 130.4(3) . . ?
O2 C6 N1 123.6(3) . . ?
O2 C6 C7 132.1(3) . . ?
N1 C6 C7 104.3(3) . . ?
C6 C7 C9 122.0(3) . . ?
C8 C7 C6 109.3(3) . . ?
C8 C7 C9 128.5(3) . . ?
N2 C8 C10 120.6(3) . . ?
C7 C8 N2 108.3(3) . . ?
C7 C8 C10 131.0(3) . . ?
C11 C10 C8 122.6(3) . . ?
C10 C11 C12 126.5(3) . . ?
C13 C12 C11 123.7(3) . . ?
C13 C12 C17 116.6(3) . . ?
C17 C12 C11 119.7(3) . . ?
C14 C13 C12 122.5(3) . . ?
C13 C14 C15 121.0(3) . . ?
N3 C15 C14 121.0(3) . . ?
N3 C15 C16 121.9(3) . . ?
C14 C15 C16 117.1(3) . . ?
C17 C16 C15 121.0(3) . . ?
C16 C17 C12 121.9(3) . . ?
N2' N1' C1' 109.9(3) . . ?
N2' N1' C6' 109.7(2) . . ?
C6' N1' C1' 139.8(3) . . ?
N1' N2' C3' 108.5(2) . . ?
N1' N2' C8' 109.1(3) . . ?
C8' N2' C3' 141.9(3) . . ?
C15' N3' C18' 120.9(3) . . ?
C15' N3' C19' 121.4(3) . . ?
C18' N3' C19' 117.6(3) . . ?
O1' C1' N1' 124.5(3) . . ?
O1' C1' C2' 131.7(3) . . ?
N1' C1' C2' 103.7(3) . . ?
C1' C2' C4' 122.7(3) . . ?
C3' C2' C1' 109.1(3) . . ?
C3' C2' C4' 128.1(3) . . ?
N2' C3' C5' 122.2(3) . . ?
C2' C3' N2' 108.7(3) . . ?
C2' C3' C5' 129.1(3) . . ?
O2' C6' N1' 124.2(3) . . ?
O2' C6' C7' 131.5(3) . . ?
N1' C6' C7' 104.2(3) . . ?
C6' C7' C9' 121.2(3) . . ?
C8' C7' C6' 109.1(3) . . ?
C8' C7' C9' 129.1(3) . . ?
N2' C8' C10' 120.6(3) . . ?
C7' C8' N2' 107.8(3) . . ?
C7' C8' C10' 131.6(3) . . ?
C11' C10' C8' 124.1(3) . . ?
C10' C11' C12' 126.1(3) . . ?
C13' C12' C11' 123.4(3) . . ?
C13' C12' C17' 116.7(3) . . ?
C17' C12' C11' 119.9(3) . . ?
C14' C13' C12' 122.0(3) . . ?
C13' C14' C15' 121.3(3) . . ?
N3' C15' C14' 120.7(3) . . ?
N3' C15' C16' 122.7(3) . . ?
C16' C15' C14' 116.5(3) . . ?
C17' C16' C15' 121.1(3) . . ?
C16' C17' C12' 122.3(3) . . ?

_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 1.551
_oxdiff_exptl_absorpt_empirical_full_min 0.717
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.4921(16) 13715 21571 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.5079(16) 13851 21571 nmt -1.0008 -0.0007 -0.0131 0.0040 -0.9992 -0.0016
0.0008 -0.0181 0.9996

_twin_special_details            
;
Component 2 rotated by 179.9063° 
around [-0.01 -0.00 1.00] (reciprocal) or [0.00 -0.01 1.00] (direct)
;
