# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_exp_1053
_database_code_depnum_ccdc_archive 'CCDC 1864261'
_audit_update_record             
;
2018-08-28 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;
_audit_creation_date             2017-12-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H11 F5 N2 O2'
_chemical_formula_sum            'C19 H11 F5 N2 O2'
_chemical_formula_weight         394.30
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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           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                   12.1293(6)
_cell_length_b                   8.5068(4)
_cell_length_c                   15.8667(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.925(5)
_cell_angle_gamma                90
_cell_volume                     1635.02(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2889
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0620
_cell_measurement_theta_min      2.9120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8760
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.521
_diffrn_reflns_theta_min         2.571
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  21.00   1.00    6.00    --  -11.59 -77.00-150.00  108
  2  ω     34.00  69.00   1.00    6.00    --   11.74  37.00 -60.00   35
  3  ω    -10.00  53.00   1.00    6.00    --   11.74 -99.00   0.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0162540000
_diffrn_orient_matrix_UB_12      -0.0068018000
_diffrn_orient_matrix_UB_13      -0.0434138000
_diffrn_orient_matrix_UB_21      0.0054632000
_diffrn_orient_matrix_UB_22      0.0824819000
_diffrn_orient_matrix_UB_23      -0.0047026000
_diffrn_orient_matrix_UB_31      0.0560417000
_diffrn_orient_matrix_UB_32      -0.0099929000
_diffrn_orient_matrix_UB_33      -0.0097025000
_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              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2918
_reflns_number_total             3905
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3905
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.032
_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)+(0.0420P)²+0.6720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1188
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C18(H18), C16(H16), C9(H9), C6(H6), C10(H10), C11(H11), C3(H3),
 C14(H14), C15(H15), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F1 F 0.47417(8) 0.84976(12) 0.59610(8) 0.0299(3) Uani 1 1 d . . . . .
F2 F 0.82794(10) 0.95478(14) 0.50288(8) 0.0391(3) Uani 1 1 d . . . . .
F4 F -0.02656(10) 0.69910(15) 0.89004(8) 0.0390(3) Uani 1 1 d . . . . .
F5 F 0.13278(10) 0.78078(16) 0.93398(7) 0.0391(3) Uani 1 1 d . . . . .
F3 F 0.01308(12) 0.94298(15) 0.88165(8) 0.0477(4) Uani 1 1 d . . . . .
O2 O 0.32200(10) 0.57017(14) 0.68627(9) 0.0253(3) Uani 1 1 d . . . . .
O1 O 0.58804(10) 0.30319(15) 0.60719(9) 0.0287(3) Uani 1 1 d . . . . .
N2 N 0.23568(12) 0.34504(18) 0.72871(10) 0.0228(4) Uani 1 1 d . . . . .
N1 N 0.51063(12) 0.54595(17) 0.60830(10) 0.0213(3) Uani 1 1 d . . . . .
H1 H 0.450472 0.594304 0.618455 0.026 Uiso 1 1 calc R . . . .
C8 C 0.41364(14) 0.3257(2) 0.66784(11) 0.0200(4) Uani 1 1 d . . . . .
C17 C 0.09618(14) 0.7724(2) 0.78683(11) 0.0182(4) Uani 1 1 d . . . . .
C12 C 0.32175(14) 0.4089(2) 0.69506(12) 0.0207(4) Uani 1 1 d . . . . .
C18 C 0.18980(14) 0.6809(2) 0.77866(12) 0.0198(4) Uani 1 1 d . . . . .
H18 H 0.227881 0.638609 0.825723 0.024 Uiso 1 1 calc R . . . .
C16 C 0.03962(14) 0.8369(2) 0.71672(12) 0.0222(4) Uani 1 1 d . . . . .
H16 H -0.023632 0.896560 0.723125 0.027 Uiso 1 1 calc R . . . .
C1 C 0.59444(14) 0.6391(2) 0.57648(11) 0.0198(4) Uani 1 1 d . . . . .
C9 C 0.41100(15) 0.1647(2) 0.68022(12) 0.0232(4) Uani 1 1 d . . . . .
H9 H 0.470045 0.103371 0.664608 0.028 Uiso 1 1 calc R . . . .
C13 C 0.22445(14) 0.6547(2) 0.69832(12) 0.0207(4) Uani 1 1 d . . . . .
C7 C 0.51207(14) 0.3899(2) 0.62513(12) 0.0206(4) Uani 1 1 d . . . . .
C2 C 0.57503(14) 0.7997(2) 0.57267(12) 0.0220(4) Uani 1 1 d . . . . .
C6 C 0.69656(15) 0.5862(2) 0.55158(12) 0.0249(4) Uani 1 1 d . . . . .
H6 H 0.712446 0.479230 0.552122 0.030 Uiso 1 1 calc R . . . .
C19 C 0.05417(16) 0.7990(2) 0.87237(13) 0.0254(4) Uani 1 1 d . . . . .
C10 C 0.32169(16) 0.0940(2) 0.71550(13) 0.0261(4) Uani 1 1 d . . . . .
H10 H 0.319606 -0.014174 0.723569 0.031 Uiso 1 1 calc R . . . .
C11 C 0.23616(16) 0.1880(2) 0.73830(12) 0.0245(4) Uani 1 1 d . . . . .
H11 H 0.175583 0.140692 0.761517 0.029 Uiso 1 1 calc R . . . .
C3 C 0.64989(15) 0.9082(2) 0.54806(12) 0.0250(4) Uani 1 1 d . . . . .
H3 H 0.633912 1.015116 0.546456 0.030 Uiso 1 1 calc R . . . .
C14 C 0.17131(15) 0.7193(2) 0.62811(12) 0.0246(4) Uani 1 1 d . . . . .
H14 H 0.197378 0.701515 0.574828 0.030 Uiso 1 1 calc R . . . .
C15 C 0.07815(15) 0.8115(2) 0.63749(12) 0.0255(4) Uani 1 1 d . . . . .
H15 H 0.041741 0.856139 0.590350 0.031 Uiso 1 1 calc R . . . .
C4 C 0.75064(16) 0.8502(2) 0.52569(13) 0.0263(4) Uani 1 1 d . . . . .
C5 C 0.77467(15) 0.6933(2) 0.52593(13) 0.0274(4) Uani 1 1 d . . . . .
H5 H 0.842787 0.658424 0.509065 0.033 Uiso 1 1 calc R . . . .


_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
F1 C2 1.365(2) . ?
F2 C4 1.355(2) . ?
F4 C19 1.337(2) . ?
F5 C19 1.339(2) . ?
F3 C19 1.334(2) . ?
O2 C12 1.379(2) . ?
O2 C13 1.406(2) . ?
O1 C7 1.225(2) . ?
N2 C12 1.314(2) . ?
N2 C11 1.345(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.403(2) . ?
N1 C7 1.354(2) . ?
C8 C12 1.407(2) . ?
C8 C9 1.384(2) . ?
C8 C7 1.505(2) . ?
C17 C18 1.388(2) . ?
C17 C16 1.389(3) . ?
C17 C19 1.491(3) . ?
C18 H18 0.9300 . ?
C18 C13 1.381(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.380(3) . ?
C1 C2 1.387(2) . ?
C1 C6 1.394(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(3) . ?
C13 C14 1.373(3) . ?
C2 C3 1.366(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.390(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(3) . ?
C11 H11 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.381(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.390(3) . ?
C15 H15 0.9300 . ?
C4 C5 1.366(3) . ?
C5 H5 0.9300 . ?

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
C12 O2 C13 119.27(13) . . ?
C12 N2 C11 117.24(16) . . ?
C1 N1 H1 115.8 . . ?
C7 N1 H1 115.8 . . ?
C7 N1 C1 128.49(15) . . ?
C12 C8 C7 127.95(16) . . ?
C9 C8 C12 115.45(16) . . ?
C9 C8 C7 116.58(16) . . ?
C18 C17 C16 121.29(17) . . ?
C18 C17 C19 119.27(17) . . ?
C16 C17 C19 119.42(16) . . ?
O2 C12 C8 117.62(15) . . ?
N2 C12 O2 117.27(15) . . ?
N2 C12 C8 125.11(17) . . ?
C17 C18 H18 121.1 . . ?
C13 C18 C17 117.74(17) . . ?
C13 C18 H18 121.1 . . ?
C17 C16 H16 120.3 . . ?
C15 C16 C17 119.42(17) . . ?
C15 C16 H16 120.3 . . ?
C2 C1 N1 116.58(15) . . ?
C2 C1 C6 117.19(16) . . ?
C6 C1 N1 126.18(17) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.81(17) . . ?
C10 C9 H9 119.6 . . ?
C18 C13 O2 120.40(17) . . ?
C14 C13 O2 117.25(16) . . ?
C14 C13 C18 122.15(17) . . ?
O1 C7 N1 123.15(16) . . ?
O1 C7 C8 120.63(16) . . ?
N1 C7 C8 116.23(15) . . ?
F1 C2 C1 116.62(15) . . ?
F1 C2 C3 119.02(16) . . ?
C3 C2 C1 124.36(17) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.00(18) . . ?
C5 C6 H6 120.0 . . ?
F4 C19 F5 105.98(16) . . ?
F4 C19 C17 112.50(16) . . ?
F5 C19 C17 112.54(16) . . ?
F3 C19 F4 106.18(16) . . ?
F3 C19 F5 106.36(16) . . ?
F3 C19 C17 112.74(16) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.17(18) . . ?
C11 C10 H10 120.9 . . ?
N2 C11 C10 123.20(17) . . ?
N2 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C2 C3 H3 121.9 . . ?
C2 C3 C4 116.23(18) . . ?
C4 C3 H3 121.9 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.32(17) . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 120.04(18) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
F2 C4 C3 117.88(17) . . ?
F2 C4 C5 119.45(17) . . ?
C5 C4 C3 122.67(17) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.52(17) . . ?
C4 C5 H5 120.2 . . ?


_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 1.151
_oxdiff_exptl_absorpt_empirical_full_min 0.911
####################################################################### 
# 
# 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_exp_181
_database_code_depnum_ccdc_archive 'CCDC 1864263'
_audit_update_record             
;
2018-08-28 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;
_audit_creation_date             2016-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 N4 O3'
_chemical_formula_sum            'C19 H20 N4 O3'
_chemical_formula_weight         352.39
_chemical_melting_point          ?
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8860(4)
_cell_length_b                   9.5658(7)
_cell_length_c                   11.4661(7)
_cell_angle_alpha                86.429(5)
_cell_angle_beta                 79.097(5)
_cell_angle_gamma                77.958(6)
_cell_volume                     830.42(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4467
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2260
_cell_measurement_theta_min      3.9110
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.825
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5513
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.578
_diffrn_reflns_theta_min         3.927
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.9665
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00 -15.00   1.00    1.00    --  -40.98 125.00   0.00   38
  2  ω    -95.00  -8.00   1.00    1.00    --  -40.98 125.00 -90.00   87
  3  ω   -112.00 -17.00   1.00    1.00    --  -40.98 -37.00 120.00   95
  4  ω     60.00  94.00   1.00    1.00    --   40.98-125.00  90.00   34
  5  ω     54.00 120.00   1.00    1.00    --  106.95-125.00  30.00   66
  6  ω     54.00 113.00   1.00    1.00    --  106.95-125.00-120.00   59
  7  ω     88.00 114.00   1.00    1.00    --  106.95-125.00-180.00   26
  8  ω     54.00 140.00   1.00    1.00    --  106.95 -77.00-150.00   86
  9  ω     81.00 169.00   1.00    1.00    --  106.95  45.00 -60.00   88
 10  ω    107.00 133.00   1.00    1.00    --  106.95 125.00  90.00   26
 11  ω     55.00 129.00   1.00    1.00    --  106.95  15.00  60.00   74
 12  ω     40.00 140.00   1.00    1.00    --  106.95 -77.00  30.00  100
 13  ω     40.00  67.00   1.00    1.00    --  106.95-125.00-180.00   27
 14  ω     33.00 134.00   1.00    1.00    --  106.95 -30.00 -30.00  101
 15  ω     34.00 134.00   1.00    1.00    --  106.95 -30.00 120.00  100
 16  ω   -108.00 -30.00   1.00    1.00    --  -40.98 -37.00-150.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0604800000
_diffrn_orient_matrix_UB_12      -0.0123866000
_diffrn_orient_matrix_UB_13      0.1354288000
_diffrn_orient_matrix_UB_21      0.1938274000
_diffrn_orient_matrix_UB_22      -0.0417937000
_diffrn_orient_matrix_UB_23      0.0161439000
_diffrn_orient_matrix_UB_31      0.0039824000
_diffrn_orient_matrix_UB_32      0.1588462000
_diffrn_orient_matrix_UB_33      0.0114346000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3112
_reflns_number_total             3233
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.088
_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)+(0.0521P)²+0.3785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1047
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B), C2(H2A,H2B), C18(H18A,H18B), C1(H1A,H1B),
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C12(H12), C13(H13), C5(H5), C14(H14), C8(H8), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.71114(13) 0.84334(11) 0.47318(8) 0.0245(2) Uani 1 1 d . . . . .
O2 O 0.09828(13) 0.49578(10) 0.68610(8) 0.0234(2) Uani 1 1 d . . . . .
O3 O 0.19184(13) 1.07637(10) 0.84379(9) 0.0234(2) Uani 1 1 d . . . . .
N4 N 0.25434(14) 0.77524(11) 0.88007(9) 0.0156(2) Uani 1 1 d . . . . .
N3 N 0.28447(14) 0.60491(12) 1.03358(9) 0.0180(2) Uani 1 1 d . . . . .
N2 N 0.31902(14) 0.62389(11) 0.65414(9) 0.0162(2) Uani 1 1 d . . . . .
H2 H 0.3908 0.6539 0.6898 0.019 Uiso 1 1 calc R . . . .
N1 N 0.60818(15) 0.74111(12) 0.64752(10) 0.0201(2) Uani 1 1 d . . . . .
C9 C 0.33300(17) 0.65737(13) 0.53208(11) 0.0156(3) Uani 1 1 d . . . . .
C15 C 0.25324(16) 0.63451(13) 0.92322(11) 0.0149(3) Uani 1 1 d . . . . .
C11 C 0.22200(16) 0.53084(13) 0.85177(11) 0.0149(3) Uani 1 1 d . . . . .
C3 C 0.59544(16) 0.76867(13) 0.53935(11) 0.0163(3) Uani 1 1 d . . . . .
C10 C 0.20522(16) 0.54937(13) 0.72306(11) 0.0159(3) Uani 1 1 d . . . . .
C12 C 0.20426(16) 0.39860(13) 0.90444(11) 0.0174(3) Uani 1 1 d . . . . .
H12 H 0.1732 0.3305 0.8626 0.021 Uiso 1 1 calc R . . . .
C13 C 0.23313(17) 0.36891(13) 1.01957(11) 0.0191(3) Uani 1 1 d . . . . .
H13 H 0.2220 0.2810 1.0562 0.023 Uiso 1 1 calc R . . . .
C5 C 0.48476(18) 0.76115(14) 0.35352(11) 0.0200(3) Uani 1 1 d . . . . .
H5 H 0.5757 0.8053 0.3159 0.024 Uiso 1 1 calc R . . . .
C14 C 0.27884(17) 0.47285(14) 1.07878(11) 0.0196(3) Uani 1 1 d . . . . .
H14 H 0.3072 0.4502 1.1537 0.024 Uiso 1 1 calc R . . . .
C4 C 0.46833(16) 0.72848(13) 0.47548(11) 0.0163(3) Uani 1 1 d . . . . .
C8 C 0.21575(17) 0.62579(14) 0.46443(12) 0.0191(3) Uani 1 1 d . . . . .
H8 H 0.1257 0.5797 0.5003 0.023 Uiso 1 1 calc R . . . .
C6 C 0.36800(19) 0.72882(15) 0.28804(12) 0.0225(3) Uani 1 1 d . . . . .
H6 H 0.3801 0.7512 0.2072 0.027 Uiso 1 1 calc R . . . .
C16 C 0.09156(17) 0.85389(13) 0.84291(12) 0.0182(3) Uani 1 1 d . . . . .
H16A H 0.0007 0.8795 0.9122 0.022 Uiso 1 1 calc R . . . .
H16B H 0.0501 0.7940 0.7938 0.022 Uiso 1 1 calc R . . . .
C19 C 0.31970(18) 0.86600(14) 0.95207(12) 0.0198(3) Uani 1 1 d . . . . .
H19A H 0.4297 0.8154 0.9739 0.024 Uiso 1 1 calc R . . . .
H19B H 0.2347 0.8913 1.0243 0.024 Uiso 1 1 calc R . . . .
C2 C 0.81213(18) 0.88233(15) 0.55477(12) 0.0217(3) Uani 1 1 d . . . . .
H2A H 0.7804 0.9841 0.5694 0.026 Uiso 1 1 calc R . . . .
H2B H 0.9376 0.8568 0.5241 0.026 Uiso 1 1 calc R . . . .
C18 C 0.34825(19) 0.99948(14) 0.87955(13) 0.0222(3) Uani 1 1 d . . . . .
H18A H 0.3916 1.0608 0.9263 0.027 Uiso 1 1 calc R . . . .
H18B H 0.4375 0.9729 0.8096 0.027 Uiso 1 1 calc R . . . .
C7 C 0.23288(18) 0.66275(15) 0.34431(12) 0.0216(3) Uani 1 1 d . . . . .
H7 H 0.1525 0.6429 0.3010 0.026 Uiso 1 1 calc R . . . .
C1 C 0.76123(17) 0.79545(15) 0.66799(12) 0.0213(3) Uani 1 1 d . . . . .
H1A H 0.8574 0.7173 0.6796 0.026 Uiso 1 1 calc R . . . .
H1B H 0.7301 0.8554 0.7371 0.026 Uiso 1 1 calc R . . . .
C17 C 0.12779(19) 0.98789(14) 0.77347(13) 0.0222(3) Uani 1 1 d . . . . .
H17A H 0.2144 0.9616 0.7022 0.027 Uiso 1 1 calc R . . . .
H17B H 0.0202 1.0406 0.7496 0.027 Uiso 1 1 calc R . . . .


_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 C3 1.3642(15) . ?
O1 C2 1.4484(16) . ?
O2 C10 1.2232(16) . ?
O3 C18 1.4162(17) . ?
O3 C17 1.4280(16) . ?
N4 C15 1.4062(16) . ?
N4 C16 1.4695(16) . ?
N4 C19 1.4623(16) . ?
N3 C15 1.3365(17) . ?
N3 C14 1.3415(17) . ?
N2 H2 0.8600 . ?
N2 C9 1.4050(16) . ?
N2 C10 1.3662(16) . ?
N1 C3 1.2701(17) . ?
N1 C1 1.4718(16) . ?
C9 C4 1.4173(18) . ?
C9 C8 1.4017(18) . ?
C15 C11 1.4123(17) . ?
C11 C10 1.5029(17) . ?
C11 C12 1.3897(17) . ?
C3 C4 1.4705(18) . ?
C12 H12 0.9300 . ?
C12 C13 1.3839(18) . ?
C13 H13 0.9300 . ?
C13 C14 1.3804(19) . ?
C5 H5 0.9300 . ?
C5 C4 1.4013(18) . ?
C5 C6 1.3843(19) . ?
C14 H14 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.3889(18) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.5159(17) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.5130(18) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.5312(18) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C7 H7 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
C3 O1 C2 105.98(10) . . ?
C18 O3 C17 109.74(10) . . ?
C15 N4 C16 116.25(10) . . ?
C15 N4 C19 116.16(10) . . ?
C19 N4 C16 110.09(10) . . ?
C15 N3 C14 118.12(11) . . ?
C9 N2 H2 116.1 . . ?
C10 N2 H2 116.1 . . ?
C10 N2 C9 127.84(11) . . ?
C3 N1 C1 106.91(11) . . ?
N2 C9 C4 118.90(11) . . ?
C8 C9 N2 122.48(12) . . ?
C8 C9 C4 118.60(11) . . ?
N4 C15 C11 120.88(11) . . ?
N3 C15 N4 116.64(11) . . ?
N3 C15 C11 122.48(11) . . ?
C15 C11 C10 126.27(11) . . ?
C12 C11 C15 117.59(11) . . ?
C12 C11 C10 116.15(11) . . ?
O1 C3 C4 115.16(11) . . ?
N1 C3 O1 117.71(12) . . ?
N1 C3 C4 127.13(12) . . ?
O2 C10 N2 124.57(12) . . ?
O2 C10 C11 119.95(11) . . ?
N2 C10 C11 115.45(11) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.58(12) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.8 . . ?
C14 C13 C12 118.47(11) . . ?
C14 C13 H13 120.8 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C6 C5 C4 121.13(13) . . ?
N3 C14 C13 123.28(12) . . ?
N3 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
C9 C4 C3 122.64(11) . . ?
C5 C4 C9 119.44(12) . . ?
C5 C4 C3 117.92(12) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 C9 120.56(12) . . ?
C7 C8 H8 119.7 . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.28(12) . . ?
C7 C6 H6 120.4 . . ?
N4 C16 H16A 109.8 . . ?
N4 C16 H16B 109.8 . . ?
N4 C16 C17 109.33(10) . . ?
H16A C16 H16B 108.3 . . ?
C17 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
N4 C19 H19A 110.1 . . ?
N4 C19 H19B 110.1 . . ?
N4 C19 C18 108.19(10) . . ?
H19A C19 H19B 108.4 . . ?
C18 C19 H19A 110.1 . . ?
C18 C19 H19B 110.1 . . ?
O1 C2 H2A 111.0 . . ?
O1 C2 H2B 111.0 . . ?
O1 C2 C1 103.61(10) . . ?
H2A C2 H2B 109.0 . . ?
C1 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
O3 C18 C19 112.34(11) . . ?
O3 C18 H18A 109.1 . . ?
O3 C18 H18B 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C8 C7 H7 119.5 . . ?
C6 C7 C8 120.95(12) . . ?
C6 C7 H7 119.5 . . ?
N1 C1 C2 104.29(10) . . ?
N1 C1 H1A 110.9 . . ?
N1 C1 H1B 110.9 . . ?
C2 C1 H1A 110.9 . . ?
C2 C1 H1B 110.9 . . ?
H1A C1 H1B 108.9 . . ?
O3 C17 C16 110.63(11) . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?

_shelx_SHELXL_version_number     2014/7

_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 1.138
_oxdiff_exptl_absorpt_empirical_full_min 0.858
####################################################################### 
# 
# 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_54-1
_database_code_depnum_ccdc_archive 'CCDC 1867348'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;
_audit_creation_date             2018-09-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 Cl N3 O3'
_chemical_formula_sum            'C21 H16 Cl N3 O3'
_chemical_formula_weight         393.82
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0444(10)
_cell_length_b                   10.7234(12)
_cell_length_c                   11.5467(13)
_cell_angle_alpha                71.104(10)
_cell_angle_beta                 70.410(11)
_cell_angle_gamma                73.474(10)
_cell_volume                     870.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4164
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.0600
_cell_measurement_theta_min      2.7150
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11524
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.586
_diffrn_reflns_theta_min         2.048
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00  21.00   1.00    2.00    --  -11.59 -77.00  60.00  109
  2  ω    -60.00  40.00   1.00    2.00    --   11.74 -57.00-180.00  100
  3  ω    -20.00  53.00   1.00    2.00    --   11.74 -99.00-180.00   73
  4  ω    -16.00  85.00   1.00    2.00    --   11.74  57.00 -30.00  101
  5  ω    -86.00 -47.00   1.00    2.00    --  -11.59 -37.00 150.00   39
  6  ω    -20.00  53.00   1.00    2.00    --   11.74 -99.00   0.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0845227000
_diffrn_orient_matrix_UB_12      0.0148201000
_diffrn_orient_matrix_UB_13      -0.0086707000
_diffrn_orient_matrix_UB_21      -0.0342412000
_diffrn_orient_matrix_UB_22      0.0209335000
_diffrn_orient_matrix_UB_23      0.0573191000
_diffrn_orient_matrix_UB_31      0.0282393000
_diffrn_orient_matrix_UB_32      -0.0665426000
_diffrn_orient_matrix_UB_33      0.0343716000
_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              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3235
_reflns_number_total             4192
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0561
_refine_ls_restrained_S_all      1.037
_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)+(0.0589P)²+0.4737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1414
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C12(H12), C17(H17), C4(H4), C19(H19), C2(H2A), C21(H21),
 C18(H18), C11(H11), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl1 Cl 0.73997(9) 0.46317(6) 1.06349(6) 0.03406(19) Uani 1 1 d . . . . .
O1 O 0.62787(19) 0.82889(16) 0.67171(13) 0.0227(3) Uani 1 1 d . . . . .
O2 O 0.5675(2) 0.83826(16) 0.32136(14) 0.0253(4) Uani 1 1 d . . . . .
O3 O 1.2823(2) 0.55913(16) 0.49394(15) 0.0272(4) Uani 1 1 d . . . . .
N2 N 0.7768(2) 0.79037(17) 0.43080(16) 0.0191(4) Uani 1 1 d . . . . .
H2 H 0.790966 0.776857 0.504783 0.023 Uiso 1 1 calc R . . . .
N1 N 0.3226(2) 0.84432(18) 0.75764(17) 0.0214(4) Uani 1 1 d . . . . .
N3 N 0.9898(2) 0.63054(18) 0.58820(17) 0.0213(4) Uani 1 1 d . . . . .
C7 C 0.9333(3) 0.7762(2) 0.3296(2) 0.0189(4) Uani 1 1 d . . . . .
C6 C 0.6047(3) 0.8239(2) 0.4202(2) 0.0187(4) Uani 1 1 d . . . . .
C16 C 0.6478(3) 0.7979(2) 0.7949(2) 0.0210(5) Uani 1 1 d . . . . .
C1 C 0.4621(3) 0.8374(2) 0.6575(2) 0.0190(4) Uani 1 1 d . . . . .
C13 C 1.1145(3) 0.6294(2) 0.4853(2) 0.0195(4) Uani 1 1 d . . . . .
C3 C 0.1304(3) 0.8734(2) 0.6263(2) 0.0232(5) Uani 1 1 d . . . . .
H3 H 0.014628 0.888764 0.618092 0.028 Uiso 1 1 calc R . . . .
C5 C 0.4525(3) 0.8406(2) 0.53705(19) 0.0179(4) Uani 1 1 d . . . . .
C8 C 1.0985(3) 0.6993(2) 0.3556(2) 0.0204(4) Uani 1 1 d . . . . .
C12 C 0.9310(3) 0.8406(2) 0.2031(2) 0.0206(4) Uani 1 1 d . . . . .
H12 H 0.824143 0.892419 0.185107 0.025 Uiso 1 1 calc R . . . .
C17 C 0.6545(3) 0.8989(2) 0.8418(2) 0.0229(5) Uani 1 1 d . . . . .
H17 H 0.634449 0.988392 0.796290 0.028 Uiso 1 1 calc R . . . .
C4 C 0.2796(3) 0.8621(2) 0.5237(2) 0.0200(4) Uani 1 1 d . . . . .
H4 H 0.264556 0.868885 0.445323 0.024 Uiso 1 1 calc R . . . .
C14 C 1.0712(3) 0.5495(2) 0.6931(2) 0.0225(5) Uani 1 1 d . . . . .
H14A H 1.021311 0.468956 0.737155 0.027 Uiso 1 1 calc R . . . .
H14B H 1.050872 0.600927 0.753602 0.027 Uiso 1 1 calc R . . . .
C19 C 0.7206(3) 0.7298(2) 1.0280(2) 0.0234(5) Uani 1 1 d . . . . .
H19 H 0.745720 0.707055 1.106059 0.028 Uiso 1 1 calc R . . . .
C2 C 0.1588(3) 0.8611(2) 0.7412(2) 0.0229(5) Uani 1 1 d . . . . .
H2A H 0.059255 0.864664 0.811225 0.028 Uiso 1 1 calc R . . . .
C21 C 0.6733(3) 0.6630(2) 0.8618(2) 0.0230(5) Uani 1 1 d . . . . .
H21 H 0.665505 0.596434 0.829584 0.028 Uiso 1 1 calc R . . . .
C18 C 0.6918(3) 0.8639(2) 0.9581(2) 0.0243(5) Uani 1 1 d . . . . .
H18 H 0.697894 0.930923 0.990468 0.029 Uiso 1 1 calc R . . . .
C11 C 1.0851(3) 0.8278(2) 0.1055(2) 0.0233(5) Uani 1 1 d . . . . .
H11 H 1.080723 0.870539 0.022185 0.028 Uiso 1 1 calc R . . . .
C20 C 0.7106(3) 0.6316(2) 0.9781(2) 0.0223(5) Uani 1 1 d . . . . .
C15 C 1.2719(3) 0.5137(2) 0.6284(2) 0.0241(5) Uani 1 1 d . . . . .
H15A H 1.340764 0.559658 0.650076 0.029 Uiso 1 1 calc R . . . .
H15B H 1.316681 0.417517 0.652907 0.029 Uiso 1 1 calc R . . . .
C9 C 1.2534(3) 0.6898(2) 0.2539(2) 0.0248(5) Uani 1 1 d . . . . .
H9 H 1.362270 0.640660 0.270336 0.030 Uiso 1 1 calc R . . . .
C10 C 1.2473(3) 0.7520(2) 0.1297(2) 0.0267(5) Uani 1 1 d . . . . .
H10 H 1.350608 0.743202 0.063065 0.032 Uiso 1 1 calc R . . . .


_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
Cl1 C20 1.747(2) . ?
O1 C16 1.405(2) . ?
O1 C1 1.371(2) . ?
O2 C6 1.227(2) . ?
O3 C13 1.365(2) . ?
O3 C15 1.450(3) . ?
N2 H2 0.8600 . ?
N2 C7 1.412(3) . ?
N2 C6 1.364(3) . ?
N1 C1 1.319(3) . ?
N1 C2 1.348(3) . ?
N3 C13 1.273(3) . ?
N3 C14 1.476(3) . ?
C7 C8 1.421(3) . ?
C7 C12 1.403(3) . ?
C6 C5 1.508(3) . ?
C16 C17 1.379(3) . ?
C16 C21 1.394(3) . ?
C1 C5 1.408(3) . ?
C13 C8 1.472(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(3) . ?
C3 C2 1.379(3) . ?
C5 C4 1.396(3) . ?
C8 C9 1.402(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.375(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(3) . ?
C4 H4 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.529(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.399(3) . ?
C19 C20 1.385(3) . ?
C2 H2A 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.388(3) . ?
C18 H18 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.392(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C9 H9 0.9300 . ?
C9 C10 1.383(3) . ?
C10 H10 0.9300 . ?

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
C1 O1 C16 118.90(16) . . ?
C13 O3 C15 106.01(16) . . ?
C7 N2 H2 117.5 . . ?
C6 N2 H2 117.5 . . ?
C6 N2 C7 125.03(18) . . ?
C1 N1 C2 117.15(19) . . ?
C13 N3 C14 106.93(17) . . ?
N2 C7 C8 119.84(18) . . ?
C12 C7 N2 121.24(18) . . ?
C12 C7 C8 118.88(19) . . ?
O2 C6 N2 123.4(2) . . ?
O2 C6 C5 118.39(18) . . ?
N2 C6 C5 118.23(18) . . ?
C17 C16 O1 119.64(19) . . ?
C17 C16 C21 122.29(19) . . ?
C21 C16 O1 117.90(19) . . ?
O1 C1 C5 117.88(18) . . ?
N1 C1 O1 117.39(18) . . ?
N1 C1 C5 124.72(19) . . ?
O3 C13 C8 115.51(18) . . ?
N3 C13 O3 117.75(19) . . ?
N3 C13 C8 126.73(19) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C2 C3 C4 117.88(19) . . ?
C1 C5 C6 128.43(18) . . ?
C4 C5 C6 115.67(18) . . ?
C4 C5 C1 115.90(19) . . ?
C7 C8 C13 122.78(19) . . ?
C9 C8 C7 118.87(19) . . ?
C9 C8 C13 118.35(19) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.7(2) . . ?
C11 C12 H12 119.6 . . ?
C16 C17 H17 120.8 . . ?
C16 C17 C18 118.4(2) . . ?
C18 C17 H17 120.8 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N3 C14 H14A 110.8 . . ?
N3 C14 H14B 110.8 . . ?
N3 C14 C15 104.54(17) . . ?
H14A C14 H14B 108.9 . . ?
C15 C14 H14A 110.8 . . ?
C15 C14 H14B 110.8 . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C20 C19 C18 118.4(2) . . ?
N1 C2 C3 123.7(2) . . ?
N1 C2 H2A 118.2 . . ?
C3 C2 H2A 118.2 . . ?
C16 C21 H21 121.1 . . ?
C20 C21 C16 117.7(2) . . ?
C20 C21 H21 121.1 . . ?
C17 C18 C19 121.4(2) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C12 C11 H11 119.5 . . ?
C12 C11 C10 120.9(2) . . ?
C10 C11 H11 119.5 . . ?
C19 C20 Cl1 120.07(17) . . ?
C19 C20 C21 121.9(2) . . ?
C21 C20 Cl1 118.03(17) . . ?
O3 C15 C14 104.01(16) . . ?
O3 C15 H15A 111.0 . . ?
O3 C15 H15B 111.0 . . ?
C14 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.3(2) . . ?
C10 C9 H9 119.4 . . ?
C11 C10 H10 120.4 . . ?
C9 C10 C11 119.3(2) . . ?
C9 C10 H10 120.4 . . ?

_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 1.645
_oxdiff_exptl_absorpt_empirical_full_min 0.653
####################################################################### 
# 
# 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_exp_178
_database_code_depnum_ccdc_archive 'CCDC 1864265'
_audit_update_record             
;
2018-08-28 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;
_audit_creation_date             2016-12-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 N4 O3'
_chemical_formula_sum            'C19 H20 N4 O3'
_chemical_formula_weight         352.39
_chemical_melting_point          ?
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7358(5)
_cell_length_b                   9.6039(6)
_cell_length_c                   11.6310(7)
_cell_angle_alpha                85.647(5)
_cell_angle_beta                 76.146(5)
_cell_angle_gamma                78.816(5)
_cell_volume                     822.64(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2676
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.9370
_cell_measurement_theta_min      3.7930
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6220
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.493
_diffrn_reflns_theta_min         3.610
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.8362
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  17.00   1.00    4.49    --  -11.51 -57.00  30.00   96
  2  ω    -32.00  59.00   1.00    4.49    --  -11.51  57.00-180.00   91
  3  ω    -15.00  76.00   1.00    4.49    --   11.74  77.00 -60.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0825783000
_diffrn_orient_matrix_UB_12      0.0215525000
_diffrn_orient_matrix_UB_13      -0.0292284000
_diffrn_orient_matrix_UB_21      0.0488069000
_diffrn_orient_matrix_UB_22      -0.0661118000
_diffrn_orient_matrix_UB_23      0.0160136000
_diffrn_orient_matrix_UB_31      -0.0046103000
_diffrn_orient_matrix_UB_32      -0.0289491000
_diffrn_orient_matrix_UB_33      -0.0532752000
_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              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3126
_reflns_number_total             3834
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3834
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.033
_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)+(0.0452P)²+0.3160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1137
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C16(H16A,H16B), C19(H19A,H19B), C2(H2A,H2B), C18(H18A,H18B),
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C8(H8), C5(H5), C12(H12), C6(H6), C14(H14), C13(H13), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O2 O 0.10015(15) 0.48072(12) 0.69790(9) 0.0220(3) Uani 1 1 d . . . . .
O3 O 0.17722(15) 1.06216(11) 0.84140(9) 0.0226(3) Uani 1 1 d . . . . .
O1 O 0.71917(16) 0.85154(12) 0.47629(9) 0.0256(3) Uani 1 1 d . . . . .
N2 N 0.32853(16) 0.61022(13) 0.65946(10) 0.0162(3) Uani 1 1 d . . . . .
H2 H 0.4057 0.6364 0.6917 0.019 Uiso 1 1 calc R . . . .
N1 N 0.61819(17) 0.73641(14) 0.64800(11) 0.0192(3) Uani 1 1 d . . . . .
N3 N 0.25630(17) 0.33694(14) 1.01387(11) 0.0199(3) Uani 1 1 d . . . . .
N4 N 0.24394(16) 0.76330(12) 0.88657(10) 0.0152(3) Uani 1 1 d . . . . .
C8 C 0.2241(2) 0.61572(16) 0.47533(13) 0.0187(3) Uani 1 1 d . . . . .
H8 H 0.1381 0.5607 0.5111 0.022 Uiso 1 1 calc R . . . .
C11 C 0.22683(19) 0.51609(15) 0.85793(12) 0.0146(3) Uani 1 1 d . . . . .
C3 C 0.60268(19) 0.77091(15) 0.54291(12) 0.0155(3) Uani 1 1 d . . . . .
C9 C 0.34043(19) 0.65076(15) 0.53978(12) 0.0149(3) Uani 1 1 d . . . . .
C4 C 0.47332(19) 0.73195(15) 0.48278(12) 0.0158(3) Uani 1 1 d . . . . .
C10 C 0.20969(19) 0.53422(15) 0.73166(12) 0.0152(3) Uani 1 1 d . . . . .
C5 C 0.4843(2) 0.77572(16) 0.36438(13) 0.0203(3) Uani 1 1 d . . . . .
H5 H 0.5730 0.8273 0.3264 0.024 Uiso 1 1 calc R . . . .
C12 C 0.22704(19) 0.37898(16) 0.90678(13) 0.0176(3) Uani 1 1 d . . . . .
H12 H 0.2052 0.3115 0.8614 0.021 Uiso 1 1 calc R . . . .
C15 C 0.24643(19) 0.62267(15) 0.92856(12) 0.0148(3) Uani 1 1 d . . . . .
C6 C 0.3655(2) 0.74362(17) 0.30259(13) 0.0215(3) Uani 1 1 d . . . . .
H6 H 0.3720 0.7759 0.2245 0.026 Uiso 1 1 calc R . . . .
C14 C 0.2731(2) 0.57900(16) 1.04111(13) 0.0186(3) Uani 1 1 d . . . . .
H14 H 0.2866 0.6449 1.0914 0.022 Uiso 1 1 calc R . . . .
C1 C 0.8247(2) 0.88601(17) 0.55428(13) 0.0210(3) Uani 1 1 d . . . . .
H1A H 0.7928 0.9859 0.5726 0.025 Uiso 1 1 calc R . . . .
H1B H 0.9534 0.8632 0.5188 0.025 Uiso 1 1 calc R . . . .
C13 C 0.2797(2) 0.43886(17) 1.07818(13) 0.0201(3) Uani 1 1 d . . . . .
H13 H 0.3017 0.4133 1.1528 0.024 Uiso 1 1 calc R . . . .
C16 C 0.0839(2) 0.83545(16) 0.84396(13) 0.0181(3) Uani 1 1 d . . . . .
H16A H -0.0172 0.8613 0.9108 0.022 Uiso 1 1 calc R . . . .
H16B H 0.0501 0.7721 0.7955 0.022 Uiso 1 1 calc R . . . .
C19 C 0.2974(2) 0.85992(16) 0.95781(13) 0.0191(3) Uani 1 1 d . . . . .
H19A H 0.4065 0.8141 0.9825 0.023 Uiso 1 1 calc R . . . .
H19B H 0.2022 0.8840 1.0283 0.023 Uiso 1 1 calc R . . . .
C2 C 0.7735(2) 0.79290(17) 0.66517(13) 0.0205(3) Uani 1 1 d . . . . .
H2A H 0.8733 0.7165 0.6720 0.025 Uiso 1 1 calc R . . . .
H2B H 0.7401 0.8486 0.7359 0.025 Uiso 1 1 calc R . . . .
C7 C 0.2368(2) 0.66303(17) 0.35795(13) 0.0211(3) Uani 1 1 d . . . . .
H7 H 0.1580 0.6403 0.3162 0.025 Uiso 1 1 calc R . . . .
C18 C 0.3310(2) 0.99317(16) 0.88465(14) 0.0217(3) Uani 1 1 d . . . . .
H18A H 0.3625 1.0584 0.9327 0.026 Uiso 1 1 calc R . . . .
H18B H 0.4330 0.9688 0.8180 0.026 Uiso 1 1 calc R . . . .
C17 C 0.1270(2) 0.96721(16) 0.77198(13) 0.0208(3) Uani 1 1 d . . . . .
H17A H 0.2253 0.9405 0.7037 0.025 Uiso 1 1 calc R . . . .
H17B H 0.0218 1.0146 0.7435 0.025 Uiso 1 1 calc R . . . .


_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
O2 C10 1.2228(18) . ?
O3 C18 1.4274(18) . ?
O3 C17 1.4263(19) . ?
O1 C3 1.3628(18) . ?
O1 C1 1.4507(19) . ?
N2 H2 0.8600 . ?
N2 C9 1.4028(18) . ?
N2 C10 1.3714(19) . ?
N1 C3 1.2694(19) . ?
N1 C2 1.4705(19) . ?
N3 C12 1.3375(19) . ?
N3 C13 1.340(2) . ?
N4 C15 1.3990(18) . ?
N4 C16 1.4725(18) . ?
N4 C19 1.4655(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.401(2) . ?
C8 C7 1.392(2) . ?
C11 C10 1.500(2) . ?
C11 C12 1.394(2) . ?
C11 C15 1.412(2) . ?
C3 C4 1.467(2) . ?
C9 C4 1.418(2) . ?
C4 C5 1.396(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(2) . ?
C12 H12 0.9300 . ?
C15 C14 1.395(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.377(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.529(2) . ?
C13 H13 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.511(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.512(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C7 H7 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
C17 O3 C18 109.99(11) . . ?
C3 O1 C1 106.09(11) . . ?
C9 N2 H2 115.8 . . ?
C10 N2 H2 115.8 . . ?
C10 N2 C9 128.34(13) . . ?
C3 N1 C2 107.03(12) . . ?
C12 N3 C13 115.45(13) . . ?
C15 N4 C16 117.31(12) . . ?
C15 N4 C19 117.41(11) . . ?
C19 N4 C16 109.85(11) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.20(14) . . ?
C12 C11 C10 115.32(13) . . ?
C12 C11 C15 118.41(13) . . ?
C15 C11 C10 126.25(13) . . ?
O1 C3 C4 115.16(12) . . ?
N1 C3 O1 117.64(14) . . ?
N1 C3 C4 127.20(14) . . ?
N2 C9 C4 118.64(13) . . ?
C8 C9 N2 122.37(13) . . ?
C8 C9 C4 118.98(13) . . ?
C9 C4 C3 122.54(12) . . ?
C5 C4 C3 118.13(14) . . ?
C5 C4 C9 119.33(14) . . ?
O2 C10 N2 124.13(13) . . ?
O2 C10 C11 121.07(13) . . ?
N2 C10 C11 114.76(13) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.14(15) . . ?
C6 C5 H5 119.4 . . ?
N3 C12 C11 125.07(14) . . ?
N3 C12 H12 117.5 . . ?
C11 C12 H12 117.5 . . ?
N4 C15 C11 121.74(12) . . ?
C14 C15 N4 122.02(14) . . ?
C14 C15 C11 116.22(13) . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.52(14) . . ?
C7 C6 H6 120.2 . . ?
C15 C14 H14 119.8 . . ?
C13 C14 C15 120.37(14) . . ?
C13 C14 H14 119.8 . . ?
O1 C1 H1A 111.0 . . ?
O1 C1 H1B 111.0 . . ?
O1 C1 C2 103.56(12) . . ?
H1A C1 H1B 109.0 . . ?
C2 C1 H1A 111.0 . . ?
C2 C1 H1B 111.0 . . ?
N3 C13 C14 124.33(14) . . ?
N3 C13 H13 117.8 . . ?
C14 C13 H13 117.8 . . ?
N4 C16 H16A 109.8 . . ?
N4 C16 H16B 109.8 . . ?
N4 C16 C17 109.35(12) . . ?
H16A C16 H16B 108.3 . . ?
C17 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
N4 C19 H19A 109.8 . . ?
N4 C19 H19B 109.8 . . ?
N4 C19 C18 109.16(12) . . ?
H19A C19 H19B 108.3 . . ?
C18 C19 H19A 109.8 . . ?
C18 C19 H19B 109.8 . . ?
N1 C2 C1 104.48(12) . . ?
N1 C2 H2A 110.9 . . ?
N1 C2 H2B 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C8 C7 H7 119.6 . . ?
C6 C7 C8 120.80(14) . . ?
C6 C7 H7 119.6 . . ?
O3 C18 C19 112.43(13) . . ?
O3 C18 H18A 109.1 . . ?
O3 C18 H18B 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
O3 C17 C16 110.88(12) . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?

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 C9 -178.76(13) . . . . ?
O1 C3 C4 C5 2.03(19) . . . . ?
O1 C1 C2 N1 -10.75(15) . . . . ?
N2 C9 C4 C3 2.2(2) . . . . ?
N2 C9 C4 C5 -178.64(13) . . . . ?
N1 C3 C4 C9 2.2(2) . . . . ?
N1 C3 C4 C5 -177.06(14) . . . . ?
N4 C15 C14 C13 -178.23(13) . . . . ?
N4 C16 C17 O3 -59.42(16) . . . . ?
N4 C19 C18 O3 56.95(16) . . . . ?
C8 C9 C4 C3 -178.79(13) . . . . ?
C8 C9 C4 C5 0.4(2) . . . . ?
C11 C15 C14 C13 0.1(2) . . . . ?
C3 O1 C1 C2 9.43(15) . . . . ?
C3 N1 C2 C1 8.40(16) . . . . ?
C3 C4 C5 C6 -179.46(13) . . . . ?
C9 N2 C10 O2 5.3(2) . . . . ?
C9 N2 C10 C11 -176.65(13) . . . . ?
C9 C8 C7 C6 0.8(2) . . . . ?
C9 C4 C5 C6 1.3(2) . . . . ?
C4 C5 C6 C7 -2.0(2) . . . . ?
C10 N2 C9 C8 -0.1(2) . . . . ?
C10 N2 C9 C4 178.94(13) . . . . ?
C10 C11 C12 N3 173.99(13) . . . . ?
C10 C11 C15 N4 2.9(2) . . . . ?
C10 C11 C15 C14 -175.51(14) . . . . ?
C5 C6 C7 C8 0.9(2) . . . . ?
C12 N3 C13 C14 0.7(2) . . . . ?
C12 C11 C10 O2 44.18(19) . . . . ?
C12 C11 C10 N2 -133.94(14) . . . . ?
C12 C11 C15 N4 -178.73(13) . . . . ?
C12 C11 C15 C14 2.9(2) . . . . ?
C15 N4 C16 C17 -164.20(12) . . . . ?
C15 N4 C19 C18 165.99(12) . . . . ?
C15 C11 C10 O2 -137.35(15) . . . . ?
C15 C11 C10 N2 44.5(2) . . . . ?
C15 C11 C12 N3 -4.6(2) . . . . ?
C15 C14 C13 N3 -2.1(2) . . . . ?
C1 O1 C3 N1 -4.79(18) . . . . ?
C1 O1 C3 C4 176.03(12) . . . . ?
C13 N3 C12 C11 2.7(2) . . . . ?
C16 N4 C15 C11 56.38(18) . . . . ?
C16 N4 C15 C14 -125.36(15) . . . . ?
C16 N4 C19 C18 -56.56(15) . . . . ?
C19 N4 C15 C11 -169.33(13) . . . . ?
C19 N4 C15 C14 8.9(2) . . . . ?
C19 N4 C16 C17 58.30(15) . . . . ?
C2 N1 C3 O1 -2.60(18) . . . . ?
C2 N1 C3 C4 176.47(14) . . . . ?
C7 C8 C9 N2 177.56(13) . . . . ?
C7 C8 C9 C4 -1.5(2) . . . . ?
C18 O3 C17 C16 58.67(16) . . . . ?
C17 O3 C18 C19 -57.90(16) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_date_sample_data_collection 2016-12-23
_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 1.557
_oxdiff_exptl_absorpt_empirical_full_min 0.699
####################################################################### 
# 
# 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_e0-6-2-4
_database_code_depnum_ccdc_archive 'CCDC 1864262'
_audit_update_record             
;
2018-08-28 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;
_audit_creation_date             2017-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 N3 O4'
_chemical_formula_sum            'C22 H19 N3 O4'
_chemical_formula_weight         389.40
_chemical_melting_point          ?
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           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                   8.75620(10)
_cell_length_b                   23.4732(3)
_cell_length_c                   8.8632(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.210(2)
_cell_angle_gamma                90
_cell_volume                     1820.35(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5091
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.4550
_cell_measurement_theta_min      5.0310
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.894
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9852
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.984
_diffrn_reflns_theta_min         3.766
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00  15.00   0.50    0.50    --    0.00 -57.00 -60.00  190
  2  ω    -12.00  14.00   0.50    0.50    --    0.00 -38.00-150.00   52
  3  ω    -78.00 -28.00   0.50    0.50    --    0.00 -38.00-150.00  100
  4  ω      6.00  99.00   0.50    0.80    --   95.20 -30.00-150.00  186
  5  ω     13.00  90.00   0.50    0.80    --   95.20 -15.00-150.00  154
  6  ω     32.00  67.00   0.50    0.80    --   95.20 -30.00 120.00   70
  7  ω     76.00 105.00   0.50    0.80    --   95.20 -82.00 150.00   58
  8  ω      7.00 127.00   0.50    0.80    --   95.20 -82.00-150.00  240
  9  ω      8.00 108.00   0.50    0.80    --   95.20 -30.00 -60.00  200
 10  ω     13.00 111.00   0.50    0.80    --   95.20 -61.00-150.00  196
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0802339000
_diffrn_orient_matrix_UB_12      0.0111828000
_diffrn_orient_matrix_UB_13      -0.1488085000
_diffrn_orient_matrix_UB_21      0.1524073000
_diffrn_orient_matrix_UB_22      0.0094403000
_diffrn_orient_matrix_UB_23      0.0892019000
_diffrn_orient_matrix_UB_31      0.0364714000
_diffrn_orient_matrix_UB_32      -0.0639734000
_diffrn_orient_matrix_UB_33      -0.0128658000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3180
_reflns_number_total             3593
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3593
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.094
_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)+(0.0435P)²+0.5484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.0990
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C17(H17), C18(H18), C4(H4), C8(H8), C11(H11), C9(H9), C21(H21),
 C20(H20), C10(H10), C2(H2A), C3(H3)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.66800(11) 0.65487(4) 0.60124(11) 0.0306(2) Uani 1 1 d . . . . .
O4 O 0.95546(11) 0.68077(4) 1.16365(10) 0.0291(2) Uani 1 1 d . . . . .
O3 O 0.90988(11) 0.45250(4) 0.65098(10) 0.0308(2) Uani 1 1 d . . . . .
O2 O 0.43812(12) 0.59442(4) 0.22150(10) 0.0333(2) Uani 1 1 d . . . . .
N2 N 0.59709(12) 0.56122(5) 0.41241(12) 0.0237(2) Uani 1 1 d . . . . .
H2 H 0.629084 0.568201 0.503495 0.028 Uiso 1 1 calc R . . . .
N3 N 0.76252(13) 0.53095(5) 0.66631(12) 0.0277(3) Uani 1 1 d . . . . .
N1 N 0.22959(16) 0.71109(6) 0.47901(15) 0.0401(3) Uani 1 1 d . . . . .
C12 C 0.76378(14) 0.47819(6) 0.42778(14) 0.0239(3) Uani 1 1 d . . . . .
C6 C 0.49433(14) 0.59870(6) 0.34980(14) 0.0234(3) Uani 1 1 d . . . . .
C7 C 0.65676(14) 0.51218(5) 0.34409(14) 0.0229(3) Uani 1 1 d . . . . .
C19 C 0.87366(15) 0.67511(5) 1.02955(15) 0.0241(3) Uani 1 1 d . . . . .
C17 C 0.87625(15) 0.68761(6) 0.75959(15) 0.0261(3) Uani 1 1 d . . . . .
H17 H 0.925629 0.699332 0.673903 0.031 Uiso 1 1 calc R . . . .
C18 C 0.94704(15) 0.69305(6) 0.90142(15) 0.0260(3) Uani 1 1 d . . . . .
H18 H 1.044365 0.708818 0.911035 0.031 Uiso 1 1 calc R . . . .
C13 C 0.80958(14) 0.49031(6) 0.58596(15) 0.0239(3) Uani 1 1 d . . . . .
C5 C 0.44330(15) 0.64726(6) 0.44599(14) 0.0244(3) Uani 1 1 d . . . . .
C16 C 0.73119(15) 0.66450(6) 0.74746(15) 0.0260(3) Uani 1 1 d . . . . .
C4 C 0.29800(16) 0.66869(6) 0.40856(15) 0.0289(3) Uani 1 1 d . . . . .
H4 H 0.244538 0.651883 0.327506 0.035 Uiso 1 1 calc R . . . .
C1 C 0.52330(16) 0.67352(6) 0.56651(15) 0.0281(3) Uani 1 1 d . . . . .
C8 C 0.61461(15) 0.49551(6) 0.19677(15) 0.0268(3) Uani 1 1 d . . . . .
H8 H 0.544687 0.517319 0.140172 0.032 Uiso 1 1 calc R . . . .
C11 C 0.82507(16) 0.42993(6) 0.36022(16) 0.0283(3) Uani 1 1 d . . . . .
H11 H 0.896780 0.408055 0.414344 0.034 Uiso 1 1 calc R . . . .
C9 C 0.67579(16) 0.44688(6) 0.13412(15) 0.0287(3) Uani 1 1 d . . . . .
H9 H 0.645351 0.436211 0.036479 0.034 Uiso 1 1 calc R . . . .
C21 C 0.65575(16) 0.64748(6) 0.87320(16) 0.0306(3) Uani 1 1 d . . . . .
H21 H 0.557647 0.632434 0.862932 0.037 Uiso 1 1 calc R . . . .
C15 C 0.83504(16) 0.52443(6) 0.81784(15) 0.0287(3) Uani 1 1 d . . . . .
H15A H 0.758603 0.520699 0.893577 0.034 Uiso 1 1 calc R . . . .
H15B H 0.899736 0.556870 0.843029 0.034 Uiso 1 1 calc R . . . .
C20 C 0.72648(16) 0.65285(6) 1.01540(16) 0.0295(3) Uani 1 1 d . . . . .
H20 H 0.675761 0.641629 1.100763 0.035 Uiso 1 1 calc R . . . .
C14 C 0.93011(17) 0.46985(6) 0.80771(15) 0.0309(3) Uani 1 1 d . . . . .
H14A H 1.036918 0.477268 0.833551 0.037 Uiso 1 1 calc R . . . .
H14B H 0.892960 0.440746 0.874769 0.037 Uiso 1 1 calc R . . . .
C22 C 0.87962(17) 0.66588(6) 1.29809(15) 0.0318(3) Uani 1 1 d . . . . .
H22A H 0.854051 0.626112 1.295531 0.048 Uiso 1 1 calc GR . . . .
H22B H 0.787934 0.688032 1.304505 0.048 Uiso 1 1 calc GR . . . .
H22C H 0.945934 0.673498 1.384514 0.048 Uiso 1 1 calc GR . . . .
C10 C 0.78141(16) 0.41403(6) 0.21478(16) 0.0304(3) Uani 1 1 d . . . . .
H10 H 0.822578 0.381628 0.171703 0.036 Uiso 1 1 calc R . . . .
C2 C 0.45572(19) 0.71864(7) 0.64026(18) 0.0405(4) Uani 1 1 d . . . . .
H2A H 0.507278 0.737202 0.719692 0.049 Uiso 1 1 calc R . . . .
C3 C 0.3104(2) 0.73535(7) 0.59318(19) 0.0466(4) Uani 1 1 d . . . . .
H3 H 0.265744 0.765356 0.643982 0.056 Uiso 1 1 calc R . . . .


_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 C16 1.4077(15) . ?
O1 C1 1.3645(16) . ?
O4 C19 1.3703(15) . ?
O4 C22 1.4297(16) . ?
O3 C13 1.3609(16) . ?
O3 C14 1.4518(16) . ?
O2 C6 1.2256(15) . ?
N2 H2 0.8600 . ?
N2 C6 1.3613(17) . ?
N2 C7 1.4104(17) . ?
N3 C13 1.2687(17) . ?
N3 C15 1.4713(16) . ?
N1 C4 1.3299(19) . ?
N1 C3 1.339(2) . ?
C12 C7 1.4182(18) . ?
C12 C13 1.4710(18) . ?
C12 C11 1.3981(19) . ?
C6 C5 1.5018(18) . ?
C7 C8 1.3990(18) . ?
C19 C18 1.3915(19) . ?
C19 C20 1.3918(19) . ?
C17 H17 0.9300 . ?
C17 C18 1.3859(18) . ?
C17 C16 1.3815(19) . ?
C18 H18 0.9300 . ?
C5 C4 1.3961(19) . ?
C5 C1 1.3978(18) . ?
C16 C21 1.376(2) . ?
C4 H4 0.9300 . ?
C1 C2 1.389(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.3861(19) . ?
C11 H11 0.9300 . ?
C11 C10 1.3817(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(2) . ?
C21 H21 0.9300 . ?
C21 C20 1.3884(19) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.532(2) . ?
C20 H20 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C10 H10 0.9300 . ?
C2 H2A 0.9300 . ?
C2 C3 1.381(2) . ?
C3 H3 0.9300 . ?

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
C1 O1 C16 119.00(10) . . ?
C19 O4 C22 117.07(11) . . ?
C13 O3 C14 105.97(10) . . ?
C6 N2 H2 116.5 . . ?
C6 N2 C7 127.04(11) . . ?
C7 N2 H2 116.5 . . ?
C13 N3 C15 107.22(11) . . ?
C4 N1 C3 116.02(13) . . ?
C7 C12 C13 122.69(12) . . ?
C11 C12 C7 119.25(12) . . ?
C11 C12 C13 118.02(12) . . ?
O2 C6 N2 124.10(12) . . ?
O2 C6 C5 118.12(12) . . ?
N2 C6 C5 117.75(11) . . ?
N2 C7 C12 118.87(11) . . ?
C8 C7 N2 122.71(12) . . ?
C8 C7 C12 118.42(12) . . ?
O4 C19 C18 115.86(11) . . ?
O4 C19 C20 124.46(12) . . ?
C18 C19 C20 119.68(12) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 118.98(13) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 C19 120.52(12) . . ?
C17 C18 H18 119.7 . . ?
O3 C13 C12 115.17(11) . . ?
N3 C13 O3 118.09(12) . . ?
N3 C13 C12 126.72(12) . . ?
C4 C5 C6 115.27(11) . . ?
C4 C5 C1 116.61(12) . . ?
C1 C5 C6 128.12(12) . . ?
C17 C16 O1 117.53(12) . . ?
C21 C16 O1 121.00(12) . . ?
C21 C16 C17 121.29(12) . . ?
N1 C4 C5 125.52(13) . . ?
N1 C4 H4 117.2 . . ?
C5 C4 H4 117.2 . . ?
O1 C1 C5 117.68(12) . . ?
O1 C1 C2 123.18(12) . . ?
C2 C1 C5 119.07(13) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.81(13) . . ?
C9 C8 H8 119.6 . . ?
C12 C11 H11 119.3 . . ?
C10 C11 C12 121.43(13) . . ?
C10 C11 H11 119.3 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.90(13) . . ?
C10 C9 H9 119.6 . . ?
C16 C21 H21 120.1 . . ?
C16 C21 C20 119.83(13) . . ?
C20 C21 H21 120.1 . . ?
N3 C15 H15A 110.9 . . ?
N3 C15 H15B 110.9 . . ?
N3 C15 C14 104.47(11) . . ?
H15A C15 H15B 108.9 . . ?
C14 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.67(13) . . ?
C21 C20 H20 120.2 . . ?
O3 C14 C15 104.13(10) . . ?
O3 C14 H14A 110.9 . . ?
O3 C14 H14B 110.9 . . ?
C15 C14 H14A 110.9 . . ?
C15 C14 H14B 110.9 . . ?
H14A C14 H14B 108.9 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C10 C9 119.17(13) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 C1 118.62(14) . . ?
C3 C2 H2A 120.7 . . ?
N1 C3 C2 124.14(14) . . ?
N1 C3 H3 117.9 . . ?
C2 C3 H3 117.9 . . ?


_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 1.371
_oxdiff_exptl_absorpt_empirical_full_min 0.670
####################################################################### 
# 
# 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_58-3
_database_code_depnum_ccdc_archive 'CCDC 1867347'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;
_audit_creation_date             2018-09-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 Cl F N3 O3'
_chemical_formula_sum            'C21 H15 Cl F N3 O3'
_chemical_formula_weight         411.81
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_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           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                   7.3959(4)
_cell_length_b                   19.3566(12)
_cell_length_c                   12.7098(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.147(6)
_cell_angle_gamma                90
_cell_volume                     1819.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5943
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      28.9890
_cell_measurement_theta_min      2.9370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14810
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.518
_diffrn_reflns_theta_min         2.104
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  56.00   1.00    1.00    --  -11.74  57.00  60.00   95
  2  ω     41.00  68.00   1.00    1.00    --   11.90 178.00 -90.00   27
  3  ω    -15.00  75.00   1.00    1.00    --   11.90  77.00-180.00   90
  4  ω    -83.00  13.00   1.00    1.00    --  -11.74 -57.00 -90.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0082025000
_diffrn_orient_matrix_UB_12      0.0365107000
_diffrn_orient_matrix_UB_13      -0.0008516000
_diffrn_orient_matrix_UB_21      -0.0221524000
_diffrn_orient_matrix_UB_22      -0.0002196000
_diffrn_orient_matrix_UB_23      0.0540416000
_diffrn_orient_matrix_UB_31      0.0929214000
_diffrn_orient_matrix_UB_32      0.0031795000
_diffrn_orient_matrix_UB_33      0.0140247000
_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              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3648
_reflns_number_total             4489
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.048
_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)+(0.0451P)²+0.6258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1079
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C18(H18), C4(H4), C3(H3), C20(H20), C17(H17), C8(H8),
 C11(H11), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl1 Cl 1.02082(5) 0.36548(2) 0.78001(4) 0.03396(14) Uani 1 1 d . . . . .
F1 F 0.54198(13) 0.18102(5) 0.80977(8) 0.0294(2) Uani 1 1 d . . . . .
O1 O 0.71312(16) 0.44784(5) 0.70881(9) 0.0221(3) Uani 1 1 d . . . . .
O2 O 0.95179(15) 0.63555(6) 0.65305(9) 0.0243(3) Uani 1 1 d . . . . .
O3 O 0.33394(17) 0.60549(7) 0.98078(10) 0.0342(3) Uani 1 1 d . . . . .
N2 N 0.76761(17) 0.58209(6) 0.77017(10) 0.0191(3) Uani 1 1 d . . . . .
H2 H 0.709333 0.544521 0.781959 0.023 Uiso 1 1 calc R . . . .
N1 N 0.76928(17) 0.52087(7) 0.40233(11) 0.0209(3) Uani 1 1 d . . . . .
N3 N 0.45492(19) 0.53699(7) 0.85715(11) 0.0262(3) Uani 1 1 d . . . . .
C2 C 0.73033(19) 0.46963(7) 0.60706(12) 0.0167(3) Uani 1 1 d . . . . .
C6 C 0.8474(2) 0.58876(7) 0.67504(12) 0.0177(3) Uani 1 1 d . . . . .
C5 C 0.8114(2) 0.55846(8) 0.48775(13) 0.0194(3) Uani 1 1 d . . . . .
H5 H 0.856378 0.602689 0.476759 0.023 Uiso 1 1 calc R . . . .
C16 C 0.6677(2) 0.37921(7) 0.72877(12) 0.0174(3) Uani 1 1 d . . . . .
C18 C 0.4489(2) 0.28865(8) 0.74237(12) 0.0199(3) Uani 1 1 d . . . . .
H18 H 0.331607 0.272058 0.733461 0.024 Uiso 1 1 calc R . . . .
C1 C 0.79376(19) 0.53711(7) 0.59152(12) 0.0167(3) Uani 1 1 d . . . . .
C4 C 0.7099(2) 0.45674(8) 0.42065(13) 0.0200(3) Uani 1 1 d . . . . .
H4 H 0.679789 0.429277 0.362861 0.024 Uiso 1 1 calc R . . . .
C19 C 0.5848(2) 0.24662(7) 0.78082(12) 0.0189(3) Uani 1 1 d . . . . .
C3 C 0.6902(2) 0.42864(8) 0.51967(12) 0.0192(3) Uani 1 1 d . . . . .
H3 H 0.651069 0.383324 0.527777 0.023 Uiso 1 1 calc R . . . .
C21 C 0.8021(2) 0.33531(8) 0.76673(12) 0.0192(3) Uani 1 1 d . . . . .
C7 C 0.7733(2) 0.63218(8) 0.85083(12) 0.0197(3) Uani 1 1 d . . . . .
C20 C 0.7611(2) 0.26766(8) 0.79489(13) 0.0202(3) Uani 1 1 d . . . . .
H20 H 0.849286 0.237987 0.822040 0.024 Uiso 1 1 calc R . . . .
C17 C 0.4912(2) 0.35648(8) 0.71717(12) 0.0195(3) Uani 1 1 d . . . . .
H17 H 0.401442 0.386398 0.692654 0.023 Uiso 1 1 calc R . . . .
C12 C 0.6255(2) 0.63848(8) 0.91875(13) 0.0224(3) Uani 1 1 d . . . . .
C13 C 0.4703(2) 0.59062(8) 0.91435(12) 0.0214(3) Uani 1 1 d . . . . .
C8 C 0.9220(2) 0.67595(8) 0.86601(13) 0.0252(4) Uani 1 1 d . . . . .
H8 H 1.022898 0.670999 0.824138 0.030 Uiso 1 1 calc R . . . .
C11 C 0.6272(3) 0.69030(9) 0.99460(13) 0.0292(4) Uani 1 1 d . . . . .
H11 H 0.528412 0.695114 1.038121 0.035 Uiso 1 1 calc R . . . .
C14 C 0.2782(2) 0.50548(9) 0.88070(14) 0.0288(4) Uani 1 1 d . . . . .
H14A H 0.292007 0.457027 0.898619 0.035 Uiso 1 1 calc R . . . .
H14B H 0.195033 0.509596 0.821062 0.035 Uiso 1 1 calc R . . . .
C9 C 0.9202(3) 0.72673(9) 0.94313(14) 0.0317(4) Uani 1 1 d . . . . .
H9 H 1.019717 0.755657 0.952013 0.038 Uiso 1 1 calc R . . . .
C10 C 0.7726(3) 0.73490(9) 1.00684(14) 0.0341(4) Uani 1 1 d . . . . .
H10 H 0.770799 0.769773 1.057137 0.041 Uiso 1 1 calc R . . . .
C15 C 0.2116(2) 0.54673(9) 0.97435(15) 0.0305(4) Uani 1 1 d . . . . .
H15A H 0.087775 0.561830 0.962665 0.037 Uiso 1 1 calc R . . . .
H15B H 0.218341 0.519442 1.038319 0.037 Uiso 1 1 calc R . . . .


_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
Cl1 C21 1.7247(16) . ?
F1 C19 1.3612(17) . ?
O1 C2 1.3687(18) . ?
O1 C16 1.3947(17) . ?
O2 C6 1.2260(18) . ?
O3 C13 1.359(2) . ?
O3 C15 1.455(2) . ?
N2 H2 0.8600 . ?
N2 C6 1.362(2) . ?
N2 C7 1.411(2) . ?
N1 C5 1.339(2) . ?
N1 C4 1.339(2) . ?
N3 C13 1.271(2) . ?
N3 C14 1.478(2) . ?
C2 C1 1.403(2) . ?
C2 C3 1.392(2) . ?
C6 C1 1.506(2) . ?
C5 H5 0.9300 . ?
C5 C1 1.391(2) . ?
C16 C21 1.387(2) . ?
C16 C17 1.382(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(2) . ?
C18 C17 1.389(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.381(2) . ?
C19 C20 1.375(2) . ?
C3 H3 0.9300 . ?
C21 C20 1.392(2) . ?
C7 C12 1.412(2) . ?
C7 C8 1.398(2) . ?
C20 H20 0.9300 . ?
C17 H17 0.9300 . ?
C12 C13 1.475(2) . ?
C12 C11 1.391(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.385(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.523(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(3) . ?
C10 H10 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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 C16 119.52(12) . . ?
C13 O3 C15 105.55(13) . . ?
C6 N2 H2 117.5 . . ?
C6 N2 C7 124.92(13) . . ?
C7 N2 H2 117.5 . . ?
C4 N1 C5 115.78(14) . . ?
C13 N3 C14 106.90(14) . . ?
O1 C2 C1 117.23(13) . . ?
O1 C2 C3 123.77(13) . . ?
C3 C2 C1 119.00(14) . . ?
O2 C6 N2 123.94(14) . . ?
O2 C6 C1 119.21(14) . . ?
N2 C6 C1 116.75(13) . . ?
N1 C5 H5 117.2 . . ?
N1 C5 C1 125.66(14) . . ?
C1 C5 H5 117.2 . . ?
C21 C16 O1 118.23(14) . . ?
C17 C16 O1 120.95(13) . . ?
C17 C16 C21 120.71(14) . . ?
C19 C18 H18 120.8 . . ?
C19 C18 C17 118.37(14) . . ?
C17 C18 H18 120.8 . . ?
C2 C1 C6 127.08(14) . . ?
C5 C1 C2 116.62(14) . . ?
C5 C1 C6 116.29(13) . . ?
N1 C4 H4 117.8 . . ?
N1 C4 C3 124.36(15) . . ?
C3 C4 H4 117.8 . . ?
F1 C19 C18 118.41(14) . . ?
F1 C19 C20 117.80(13) . . ?
C20 C19 C18 123.76(14) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.55(14) . . ?
C4 C3 H3 120.7 . . ?
C16 C21 Cl1 119.40(12) . . ?
C16 C21 C20 120.48(14) . . ?
C20 C21 Cl1 120.12(12) . . ?
N2 C7 C12 119.42(14) . . ?
C8 C7 N2 121.92(15) . . ?
C8 C7 C12 118.67(15) . . ?
C19 C20 C21 117.13(14) . . ?
C19 C20 H20 121.4 . . ?
C21 C20 H20 121.4 . . ?
C16 C17 C18 119.53(14) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C7 C12 C13 122.28(14) . . ?
C11 C12 C7 119.31(15) . . ?
C11 C12 C13 118.39(16) . . ?
O3 C13 C12 115.46(14) . . ?
N3 C13 O3 117.98(15) . . ?
N3 C13 C12 126.54(15) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.50(17) . . ?
C9 C8 H8 119.8 . . ?
C12 C11 H11 119.2 . . ?
C10 C11 C12 121.57(17) . . ?
C10 C11 H11 119.2 . . ?
N3 C14 H14A 110.9 . . ?
N3 C14 H14B 110.9 . . ?
N3 C14 C15 104.06(14) . . ?
H14A C14 H14B 109.0 . . ?
C15 C14 H14A 110.9 . . ?
C15 C14 H14B 110.9 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.93(17) . . ?
C10 C9 H9 119.5 . . ?
C11 C10 H10 120.5 . . ?
C9 C10 C11 118.92(16) . . ?
C9 C10 H10 120.5 . . ?
O3 C15 C14 104.07(13) . . ?
O3 C15 H15A 110.9 . . ?
O3 C15 H15B 110.9 . . ?
C14 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
H15A C15 H15B 109.0 . . ?

_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 1.399
_oxdiff_exptl_absorpt_empirical_full_min 0.657
####################################################################### 
# 
# 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_x_48
_database_code_depnum_ccdc_archive 'CCDC 1864271'
_audit_update_record             
;
2018-08-28 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;
_audit_creation_date             2018-08-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H19 F6 N3 O4'
_chemical_formula_sum            'C29 H19 F6 N3 O4'
_chemical_formula_weight         587.47
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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           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                   15.9357(8)
_cell_length_b                   13.7866(8)
_cell_length_c                   11.8725(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.908(5)
_cell_angle_gamma                90
_cell_volume                     2602.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4301
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.3870
_cell_measurement_theta_min      2.5420
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13946
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.586
_diffrn_reflns_theta_min         2.267
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  96.00   1.00    2.80    --   11.74 178.00 -90.00   61
  2  ω     -2.00  40.00   1.00    2.80    --   11.74  37.00-180.00   42
  3  ω    -15.00  84.00   1.00    2.80    --   11.74  57.00  30.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0234493000
_diffrn_orient_matrix_UB_12      -0.0412804000
_diffrn_orient_matrix_UB_13      -0.0146981000
_diffrn_orient_matrix_UB_21      -0.0379281000
_diffrn_orient_matrix_UB_22      -0.0261831000
_diffrn_orient_matrix_UB_23      -0.0112117000
_diffrn_orient_matrix_UB_31      -0.0017053000
_diffrn_orient_matrix_UB_32      0.0159266000
_diffrn_orient_matrix_UB_33      -0.0569800000
_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              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4413
_reflns_number_total             6166
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6166
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0643
_refine_ls_restrained_S_all      1.205
_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)+(0.0634P)²+1.7607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1664
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid bond restraints
 C28, F6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C28 \\sim F6: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
4.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C8(H8), C27(H27), C9(H9), C26(H26), C14(H14), C2(H2A), C3(H3),
 C23(H23), C24(H24), C6(H6), C15(H15), C5(H5), C17(H17), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
F3 F 0.05036(9) 0.40832(12) 0.64493(15) 0.0448(4) Uani 1 1 d . . . . .
O3 O 0.68230(9) 0.55891(11) 0.59498(14) 0.0252(4) Uani 1 1 d . . . . .
O2 O 0.49063(9) 0.38509(12) 0.55536(14) 0.0256(4) Uani 1 1 d . . . . .
O1 O 0.43693(10) 0.45617(12) 0.76076(14) 0.0281(4) Uani 1 1 d . . . . .
O4 O 0.85615(11) 0.21923(13) 0.69992(17) 0.0375(5) Uani 1 1 d . . . . .
F2 F 0.06452(10) 0.55245(14) 0.5812(2) 0.0700(7) Uani 1 1 d . . . . .
N2 N 0.63051(11) 0.36593(13) 0.60726(15) 0.0198(4) Uani 1 1 d . . . . .
H2 H 0.672150 0.393824 0.644069 0.024 Uiso 1 1 calc R . . . .
F1 F 0.04905(10) 0.52930(15) 0.7568(2) 0.0690(7) Uani 1 1 d . . . . .
N1 N 0.61410(12) 0.66831(15) 0.70634(17) 0.0259(4) Uani 1 1 d . . . . .
N3 N 0.78542(12) 0.36004(15) 0.71104(18) 0.0276(5) Uani 1 1 d . . . . .
F5 F 0.92143(16) 0.8303(2) 0.34334(18) 0.0909(9) Uani 1 1 d . . . . .
C13 C 0.64789(14) 0.27646(16) 0.55741(18) 0.0210(5) Uani 1 1 d . . . . .
C11 C 0.61685(13) 0.58111(16) 0.65885(18) 0.0199(5) Uani 1 1 d . . . . .
C12 C 0.55583(13) 0.41382(16) 0.60437(17) 0.0182(4) Uani 1 1 d . . . . .
C22 C 0.73536(14) 0.63333(16) 0.56262(19) 0.0212(5) Uani 1 1 d . . . . .
C10 C 0.55703(13) 0.50707(16) 0.66983(18) 0.0184(4) Uani 1 1 d . . . . .
C7 C 0.49238(14) 0.52926(17) 0.73803(19) 0.0223(5) Uani 1 1 d . . . . .
C19 C 0.78784(14) 0.27476(17) 0.67016(19) 0.0236(5) Uani 1 1 d . . . . .
C1 C 0.35149(14) 0.47107(17) 0.73663(19) 0.0231(5) Uani 1 1 d . . . . .
C25 C 0.84634(14) 0.76875(17) 0.49025(19) 0.0232(5) Uani 1 1 d . . . . .
C18 C 0.72485(15) 0.22992(17) 0.58991(19) 0.0238(5) Uani 1 1 d . . . . .
C8 C 0.48718(15) 0.61890(18) 0.78980(19) 0.0257(5) Uani 1 1 d . . . . .
H8 H 0.444031 0.633281 0.836030 0.031 Uiso 1 1 calc R . . . .
F6 F 0.97783(14) 0.8445(2) 0.5057(2) 0.1084(10) Uani 1 1 d . U . . .
C27 C 0.81886(14) 0.62817(17) 0.6016(2) 0.0258(5) Uani 1 1 d . . . . .
H27 H 0.837284 0.579696 0.651898 0.031 Uiso 1 1 calc R . . . .
C9 C 0.54832(15) 0.68551(18) 0.7700(2) 0.0284(5) Uani 1 1 d . . . . .
H9 H 0.544375 0.746583 0.802487 0.034 Uiso 1 1 calc R . . . .
C26 C 0.87484(14) 0.69628(18) 0.5649(2) 0.0270(5) Uani 1 1 d . . . . .
H26 H 0.931350 0.693518 0.590035 0.032 Uiso 1 1 calc R . . . .
C14 C 0.59252(15) 0.23241(18) 0.47640(19) 0.0258(5) Uani 1 1 d . . . . .
H14 H 0.542540 0.263183 0.452367 0.031 Uiso 1 1 calc R . . . .
C2 C 0.32022(14) 0.54215(18) 0.6631(2) 0.0251(5) Uani 1 1 d . . . . .
H2A H 0.356628 0.584274 0.629456 0.030 Uiso 1 1 calc R . . . .
C3 C 0.23411(15) 0.54996(18) 0.6400(2) 0.0276(5) Uani 1 1 d . . . . .
H3 H 0.212356 0.597976 0.591345 0.033 Uiso 1 1 calc R . . . .
C23 C 0.70631(14) 0.70419(18) 0.4878(2) 0.0262(5) Uani 1 1 d . . . . .
H23 H 0.649848 0.706217 0.462297 0.031 Uiso 1 1 calc R . . . .
C4 C 0.18020(15) 0.48591(18) 0.6897(2) 0.0277(5) Uani 1 1 d . . . . .
C24 C 0.76197(15) 0.77200(18) 0.4513(2) 0.0274(5) Uani 1 1 d . . . . .
H24 H 0.743146 0.819958 0.400615 0.033 Uiso 1 1 calc R . . . .
C6 C 0.29853(15) 0.40649(19) 0.7863(2) 0.0311(6) Uani 1 1 d . . . . .
H6 H 0.320431 0.358430 0.834743 0.037 Uiso 1 1 calc R . . . .
F4 F 0.87566(17) 0.93047(15) 0.4490(3) 0.1177(12) Uani 1 1 d . . . . .
C20 C 0.86434(15) 0.37441(19) 0.7818(2) 0.0328(6) Uani 1 1 d . . . . .
H20A H 0.852790 0.394606 0.857496 0.039 Uiso 1 1 calc R . . . .
H20B H 0.899545 0.422813 0.749102 0.039 Uiso 1 1 calc R . . . .
C28 C 0.90625(18) 0.8424(2) 0.4498(2) 0.0382(6) Uani 1 1 d . U . . .
C15 C 0.61218(18) 0.14267(19) 0.4318(2) 0.0345(6) Uani 1 1 d . . . . .
H15 H 0.575246 0.114165 0.377507 0.041 Uiso 1 1 calc R . . . .
C5 C 0.21281(16) 0.41454(19) 0.7627(2) 0.0336(6) Uani 1 1 d . . . . .
H5 H 0.176643 0.371861 0.795905 0.040 Uiso 1 1 calc R . . . .
C17 C 0.74181(17) 0.13865(18) 0.5451(2) 0.0333(6) Uani 1 1 d . . . . .
H17 H 0.791500 0.106850 0.568176 0.040 Uiso 1 1 calc R . . . .
C16 C 0.68556(19) 0.0952(2) 0.4668(2) 0.0399(7) Uani 1 1 d . . . . .
H16 H 0.697153 0.034332 0.437880 0.048 Uiso 1 1 calc R . . . .
C29 C 0.08687(16) 0.4940(2) 0.6678(3) 0.0391(7) Uani 1 1 d . . . . .
C21 C 0.90645(16) 0.2748(2) 0.7834(3) 0.0368(6) Uani 1 1 d . . . . .
H21A H 0.964230 0.279824 0.763101 0.044 Uiso 1 1 calc R . . . .
H21B H 0.905765 0.245248 0.857467 0.044 Uiso 1 1 calc R . . . .


_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
F3 C29 1.337(3) . ?
O3 C11 1.365(3) . ?
O3 C22 1.400(3) . ?
O2 C12 1.222(2) . ?
O1 C7 1.379(3) . ?
O1 C1 1.387(3) . ?
O4 C19 1.358(3) . ?
O4 C21 1.451(3) . ?
F2 C29 1.335(4) . ?
N2 H2 0.8600 . ?
N2 C13 1.404(3) . ?
N2 C12 1.359(3) . ?
F1 C29 1.343(3) . ?
N1 C11 1.330(3) . ?
N1 C9 1.354(3) . ?
N3 C19 1.274(3) . ?
N3 C20 1.478(3) . ?
F5 C28 1.314(4) . ?
C13 C18 1.414(3) . ?
C13 C14 1.399(3) . ?
C11 C10 1.409(3) . ?
C12 C10 1.502(3) . ?
C22 C27 1.381(3) . ?
C22 C23 1.379(3) . ?
C10 C7 1.387(3) . ?
C7 C8 1.385(3) . ?
C19 C18 1.472(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.386(3) . ?
C25 C26 1.391(3) . ?
C25 C24 1.392(3) . ?
C25 C28 1.495(3) . ?
C18 C17 1.400(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.371(4) . ?
F6 C28 1.280(3) . ?
C27 H27 0.9300 . ?
C27 C26 1.386(3) . ?
C9 H9 0.9300 . ?
C26 H26 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.390(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.385(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.379(3) . ?
C4 C5 1.388(4) . ?
C4 C29 1.496(3) . ?
C24 H24 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.380(3) . ?
F4 C28 1.308(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.527(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(4) . ?
C5 H5 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.383(4) . ?
C16 H16 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?

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
C11 O3 C22 119.12(17) . . ?
C7 O1 C1 118.97(17) . . ?
C19 O4 C21 106.00(19) . . ?
C13 N2 H2 116.1 . . ?
C12 N2 H2 116.1 . . ?
C12 N2 C13 127.85(18) . . ?
C11 N1 C9 116.4(2) . . ?
C19 N3 C20 107.08(19) . . ?
N2 C13 C18 118.42(19) . . ?
C14 C13 N2 122.6(2) . . ?
C14 C13 C18 119.0(2) . . ?
O3 C11 C10 115.87(19) . . ?
N1 C11 O3 119.1(2) . . ?
N1 C11 C10 125.0(2) . . ?
O2 C12 N2 124.7(2) . . ?
O2 C12 C10 120.30(19) . . ?
N2 C12 C10 114.99(18) . . ?
C27 C22 O3 117.2(2) . . ?
C23 C22 O3 120.90(19) . . ?
C23 C22 C27 121.7(2) . . ?
C11 C10 C12 123.87(19) . . ?
C7 C10 C11 115.4(2) . . ?
C7 C10 C12 120.5(2) . . ?
O1 C7 C10 117.7(2) . . ?
O1 C7 C8 120.4(2) . . ?
C8 C7 C10 121.7(2) . . ?
O4 C19 C18 115.5(2) . . ?
N3 C19 O4 117.8(2) . . ?
N3 C19 C18 126.7(2) . . ?
C2 C1 O1 122.8(2) . . ?
C2 C1 C6 121.3(2) . . ?
C6 C1 O1 115.8(2) . . ?
C26 C25 C24 120.0(2) . . ?
C26 C25 C28 120.3(2) . . ?
C24 C25 C28 119.7(2) . . ?
C13 C18 C19 121.8(2) . . ?
C17 C18 C13 119.4(2) . . ?
C17 C18 C19 118.9(2) . . ?
C7 C8 H8 121.4 . . ?
C9 C8 C7 117.2(2) . . ?
C9 C8 H8 121.4 . . ?
C22 C27 H27 120.5 . . ?
C22 C27 C26 119.1(2) . . ?
C26 C27 H27 120.5 . . ?
N1 C9 C8 124.4(2) . . ?
N1 C9 H9 117.8 . . ?
C8 C9 H9 117.8 . . ?
C25 C26 H26 120.1 . . ?
C27 C26 C25 119.9(2) . . ?
C27 C26 H26 120.1 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C1 C2 H2A 120.3 . . ?
C1 C2 C3 119.3(2) . . ?
C3 C2 H2A 120.3 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C22 C23 H23 120.4 . . ?
C22 C23 C24 119.2(2) . . ?
C24 C23 H23 120.4 . . ?
C3 C4 C29 120.9(2) . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 C29 119.1(2) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 C25 120.1(2) . . ?
C23 C24 H24 120.0 . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 H6 120.5 . . ?
N3 C20 H20A 110.9 . . ?
N3 C20 H20B 110.9 . . ?
N3 C20 C21 104.1(2) . . ?
H20A C20 H20B 109.0 . . ?
C21 C20 H20A 110.9 . . ?
C21 C20 H20B 110.9 . . ?
F5 C28 C25 112.7(2) . . ?
F6 C28 F5 106.6(3) . . ?
F6 C28 C25 114.5(2) . . ?
F6 C28 F4 107.5(3) . . ?
F4 C28 F5 101.8(3) . . ?
F4 C28 C25 112.8(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.1(2) . . ?
C16 C15 H15 119.5 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C18 C17 H17 119.6 . . ?
C16 C17 C18 120.8(2) . . ?
C16 C17 H17 119.6 . . ?
C15 C16 C17 119.6(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
F3 C29 F1 105.5(2) . . ?
F3 C29 C4 112.5(2) . . ?
F2 C29 F3 106.7(2) . . ?
F2 C29 F1 106.1(2) . . ?
F2 C29 C4 112.9(2) . . ?
F1 C29 C4 112.6(2) . . ?
O4 C21 C20 104.16(19) . . ?
O4 C21 H21A 110.9 . . ?
O4 C21 H21B 110.9 . . ?
C20 C21 H21A 110.9 . . ?
C20 C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?

_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 1.193
_oxdiff_exptl_absorpt_empirical_full_min 0.879
