# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_NOR_DIC
_database_code_depnum_ccdc_archive 'CCDC 1823915'
_audit_update_record             
;
2018-02-14 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_audit_creation_date             2017-03-30
_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         'C14 H10 Cl2 N O2, C16 H19 F N3 O3'
_chemical_formula_sum            'C30 H29 Cl2 F N4 O5'
_chemical_formula_weight         615.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O F Cl'
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.7589(4)
_cell_length_b                   11.9715(5)
_cell_length_c                   16.3035(6)
_cell_angle_alpha                73.776(3)
_cell_angle_beta                 77.048(4)
_cell_angle_gamma                80.463(4)
_cell_volume                     1408.43(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5670
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      26.3750
_cell_measurement_theta_min      1.9030
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87961
_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_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14396
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.78
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  50.00   1.00   17.20    --  -27.14  57.00-120.00  116
  2  ω    -31.00  23.00   1.00   17.20    --  -27.14 -90.00   4.00   54
  3  ω    -20.00  85.00   1.00   17.20    --   28.55 -99.00  90.00  105
  4  ω     35.00 126.00   1.00   17.20    --   28.55 178.00   0.00   91
  5  ω    -10.00 105.00   1.00   17.20    --   28.55  57.00   0.00  115
  6  ω    -60.00 115.00   1.00   17.20    --   28.55 -19.00  30.00  175
  7  ω    -10.00  60.00   1.00   17.20    --   28.55  57.00 150.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0149520000
_diffrn_orient_matrix_UB_12      -0.0605766000
_diffrn_orient_matrix_UB_13      0.0200986000
_diffrn_orient_matrix_UB_21      -0.0648325000
_diffrn_orient_matrix_UB_22      0.0076169000
_diffrn_orient_matrix_UB_23      0.0369021000
_diffrn_orient_matrix_UB_31      -0.0669367000
_diffrn_orient_matrix_UB_32      -0.0112671000
_diffrn_orient_matrix_UB_33      -0.0190363000
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5032
_reflns_number_total             5764
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         2.501
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         5764
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0905
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1228P)²+6.2402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2509
_refine_ls_wR_factor_ref         0.2583
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C29) = Uanis(C28)
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), N3(H3A,H3B), C18(H18A,H18B), C11(H11A,H11B), C14(H14A,H14B),
 C12(H12A,H12B), C13(H13A,H13B)
3.b Aromatic/amide H refined with riding coordinates:
 N4(H4), C7(H7), C10(H10), C1(H1), C20(H20), C27(H27), C23(H23), C22(H22),
 C21(H21), C29(H29), C28(H28)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl2 Cl 1.21810(16) 1.02726(11) 0.78062(8) 0.0351(3) Uani 1 d . . .
Cl1 Cl 0.85587(17) 1.27439(11) 1.00936(8) 0.0361(3) Uani 1 d . . .
F1 F 1.1632(3) 0.7378(2) 0.62872(17) 0.0266(6) Uani 1 d . . .
O3 O 1.3786(3) 1.1175(2) 0.45314(18) 0.0181(6) Uani 1 d . . .
O2 O 1.4082(4) 1.3310(2) 0.39434(19) 0.0210(6) Uani 1 d . . .
H2 H 1.4247 1.2595 0.4027 0.032 Uiso 1 calc . . GR
O1 O 1.1928(4) 1.4632(3) 0.4331(2) 0.0260(7) Uani 1 d . . .
O5 O 1.3466(5) 1.2786(3) 1.0024(2) 0.0315(8) Uani 1 d . . .
N1 N 0.8891(4) 1.1994(3) 0.5954(2) 0.0147(6) Uani 1 d . . .
N2 N 0.8296(5) 0.7832(3) 0.7276(2) 0.0238(8) Uani 1 d . . .
O4 O 1.4099(6) 1.4585(3) 0.9370(2) 0.0472(11) Uani 1 d . . .
N4 N 1.1716(5) 1.2085(3) 0.8813(2) 0.0247(8) Uani 1 d . . .
H4 H 1.2384 1.1936 0.9194 0.030 Uiso 1 calc . . R
C3 C 1.2290(5) 1.1433(3) 0.4986(2) 0.0145(7) Uani 1 d . . .
C5 C 0.9576(5) 1.0814(3) 0.6057(2) 0.0138(7) Uani 1 d . . .
C4 C 1.1264(5) 1.0539(3) 0.5591(2) 0.0140(7) Uani 1 d . . .
C2 C 1.1512(5) 1.2614(3) 0.4941(2) 0.0142(7) Uani 1 d . . .
C7 C 1.1955(5) 0.9352(3) 0.5699(2) 0.0167(8) Uani 1 d . . .
H7 H 1.3077 0.9148 0.5396 0.020 Uiso 1 calc . . R
C15 C 0.7094(5) 1.2349(3) 0.6419(3) 0.0183(8) Uani 1 d . . .
H15A H 0.7009 1.3166 0.6418 0.022 Uiso 1 calc . . R
H15B H 0.6936 1.1892 0.7019 0.022 Uiso 1 calc . . R
C9 C 0.9275(5) 0.8748(3) 0.6743(2) 0.0179(8) Uani 1 d . . .
C10 C 0.8616(5) 0.9918(3) 0.6636(2) 0.0161(8) Uani 1 d . . .
H10 H 0.7511 1.0116 0.6956 0.019 Uiso 1 calc . . R
C6 C 1.2498(5) 1.3614(3) 0.4384(3) 0.0180(8) Uani 1 d . . .
C1 C 0.9864(5) 1.2833(3) 0.5417(3) 0.0164(8) Uani 1 d . . .
H1 H 0.9385 1.3609 0.5367 0.020 Uiso 1 calc . . R
C19 C 1.3633(5) 1.3509(4) 0.7907(3) 0.0191(8) Uani 1 d . . .
N3 N 0.6323(7) 0.6241(4) 0.8674(3) 0.0434(12) Uani 1 d . . .
H3A H 0.6359 0.6540 0.9118 0.052 Uiso 1 calc . . R
H3B H 0.5715 0.5611 0.8890 0.052 Uiso 1 calc . . R
C8 C 1.0980(5) 0.8511(3) 0.6244(3) 0.0183(8) Uani 1 d . . .
C16 C 0.5619(5) 1.2176(4) 0.6007(3) 0.0243(9) Uani 1 d . . .
H16A H 0.5745 1.2648 0.5419 0.036 Uiso 1 calc . . GR
H16B H 0.4486 1.2406 0.6333 0.036 Uiso 1 calc . . GR
H16C H 0.5692 1.1367 0.6010 0.036 Uiso 1 calc . . GR
C17 C 1.4148(6) 1.3522(4) 0.9372(3) 0.0254(9) Uani 1 d . . .
C20 C 1.4006(6) 1.4424(4) 0.7155(3) 0.0237(9) Uani 1 d . . .
H20 H 1.5012 1.4802 0.7066 0.028 Uiso 1 calc . . R
C18 C 1.4918(6) 1.3139(4) 0.8530(3) 0.0247(9) Uani 1 d . . .
H18A H 1.6018 1.3482 0.8255 0.030 Uiso 1 calc . . R
H18B H 1.5189 1.2295 0.8667 0.030 Uiso 1 calc . . R
C27 C 0.7371(6) 1.0906(4) 0.9829(3) 0.0298(10) Uani 1 d . . .
H27 H 0.6391 1.1005 1.0261 0.036 Uiso 1 calc . . R
C24 C 1.2104(6) 1.2965(4) 0.8047(3) 0.0224(9) Uani 1 d . . .
C23 C 1.0987(6) 1.3327(4) 0.7429(3) 0.0244(9) Uani 1 d . . .
H23 H 0.9966 1.2966 0.7514 0.029 Uiso 1 calc . . R
C22 C 1.1415(6) 1.4226(4) 0.6692(3) 0.0276(10) Uani 1 d . . .
H22 H 1.0667 1.4464 0.6287 0.033 Uiso 1 calc . . R
C25 C 1.0272(6) 1.1442(4) 0.8975(3) 0.0226(9) Uani 1 d . . .
C21 C 1.2918(7) 1.4771(4) 0.6548(3) 0.0279(10) Uani 1 d . . .
H21 H 1.3196 1.5365 0.6049 0.033 Uiso 1 calc . . R
C11 C 0.6444(6) 0.8181(4) 0.7645(3) 0.0284(10) Uani 1 d . . .
H11A H 0.5884 0.8728 0.7192 0.034 Uiso 1 calc . . R
H11B H 0.6423 0.8575 0.8092 0.034 Uiso 1 calc . . R
C29 C 0.8925(6) 0.9864(4) 0.8772(3) 0.0245(7) Uani 1 d . . .
H29 H 0.8992 0.9292 0.8476 0.029 Uiso 1 calc . . R
C26 C 0.8731(6) 1.1611(4) 0.9603(3) 0.0262(9) Uani 1 d . . .
C30 C 1.0308(6) 1.0558(4) 0.8573(3) 0.0258(9) Uani 1 d . . .
C14 C 0.9205(7) 0.6933(4) 0.7911(3) 0.0316(11) Uani 1 d . . .
H14A H 0.9290 0.7250 0.8385 0.038 Uiso 1 calc . . R
H14B H 1.0400 0.6699 0.7633 0.038 Uiso 1 calc . . R
C12 C 0.5399(7) 0.7129(5) 0.8032(3) 0.0352(12) Uani 1 d . . .
H12A H 0.4213 0.7374 0.8315 0.042 Uiso 1 calc . . R
H12B H 0.5285 0.6791 0.7574 0.042 Uiso 1 calc . . R
C13 C 0.8159(9) 0.5881(4) 0.8262(3) 0.0416(13) Uani 1 d . . .
H13A H 0.8124 0.5543 0.7791 0.050 Uiso 1 calc . . R
H13B H 0.8740 0.5292 0.8686 0.050 Uiso 1 calc . . R
C28 C 0.7528(6) 1.0009(4) 0.9371(3) 0.0245(7) Uani 1 d . . .
H28 H 0.6625 0.9528 0.9503 0.029 Uiso 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
Cl2 C30 1.747(5) . ?
Cl1 C26 1.731(5) . ?
F1 C8 1.355(4) . ?
O3 C3 1.271(5) . ?
O2 H2 0.8200 . ?
O2 C6 1.327(5) . ?
O1 C6 1.212(5) . ?
O5 C17 1.252(5) . ?
N1 C5 1.402(5) . ?
N1 C15 1.486(5) . ?
N1 C1 1.344(5) . ?
N2 C9 1.408(5) . ?
N2 C11 1.468(6) . ?
N2 C14 1.477(6) . ?
O4 C17 1.266(6) . ?
N4 H4 0.8600 . ?
N4 C24 1.400(5) . ?
N4 C25 1.399(5) . ?
C3 C4 1.447(5) . ?
C3 C2 1.431(5) . ?
C5 C4 1.398(5) . ?
C5 C10 1.407(5) . ?
C4 C7 1.410(5) . ?
C2 C6 1.492(5) . ?
C2 C1 1.365(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.351(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.518(6) . ?
C9 C10 1.386(6) . ?
C9 C8 1.420(6) . ?
C10 H10 0.9300 . ?
C1 H1 0.9300 . ?
C19 C20 1.408(6) . ?
C19 C18 1.509(6) . ?
C19 C24 1.391(6) . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
N3 C12 1.484(8) . ?
N3 C13 1.482(8) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.530(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C27 H27 0.9300 . ?
C27 C26 1.381(6) . ?
C27 C28 1.447(7) . ?
C24 C23 1.406(6) . ?
C23 H23 0.9300 . ?
C23 C22 1.390(6) . ?
C22 H22 0.9300 . ?
C22 C21 1.372(7) . ?
C25 C26 1.416(6) . ?
C25 C30 1.386(6) . ?
C21 H21 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.519(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.391(6) . ?
C29 C28 1.311(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.516(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C28 H28 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
C6 O2 H2 109.5 . . ?
C5 N1 C15 121.5(3) . . ?
C1 N1 C5 119.8(3) . . ?
C1 N1 C15 118.6(3) . . ?
C9 N2 C11 115.8(3) . . ?
C9 N2 C14 116.7(4) . . ?
C11 N2 C14 112.6(4) . . ?
C24 N4 H4 119.1 . . ?
C25 N4 H4 119.1 . . ?
C25 N4 C24 121.9(4) . . ?
O3 C3 C4 121.6(3) . . ?
O3 C3 C2 122.8(3) . . ?
C2 C3 C4 115.6(3) . . ?
N1 C5 C10 121.2(3) . . ?
C4 C5 N1 118.7(3) . . ?
C4 C5 C10 120.1(3) . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 C7 118.7(3) . . ?
C7 C4 C3 119.5(3) . . ?
C3 C2 C6 120.5(3) . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 C6 119.5(3) . . ?
C4 C7 H7 120.2 . . ?
C8 C7 C4 119.7(4) . . ?
C8 C7 H7 120.2 . . ?
N1 C15 H15A 109.1 . . ?
N1 C15 H15B 109.1 . . ?
N1 C15 C16 112.4(3) . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
N2 C9 C8 121.0(4) . . ?
C10 C9 N2 122.9(4) . . ?
C10 C9 C8 116.0(3) . . ?
C5 C10 H10 119.1 . . ?
C9 C10 C5 121.8(4) . . ?
C9 C10 H10 119.1 . . ?
O2 C6 C2 114.9(3) . . ?
O1 C6 O2 121.4(4) . . ?
O1 C6 C2 123.7(4) . . ?
N1 C1 C2 124.0(3) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C20 C19 C18 118.9(4) . . ?
C24 C19 C20 119.0(4) . . ?
C24 C19 C18 122.1(4) . . ?
H3A N3 H3B 108.1 . . ?
C12 N3 H3A 109.5 . . ?
C12 N3 H3B 109.5 . . ?
C13 N3 H3A 109.5 . . ?
C13 N3 H3B 109.5 . . ?
C13 N3 C12 110.6(4) . . ?
F1 C8 C9 118.1(3) . . ?
C7 C8 F1 118.1(4) . . ?
C7 C8 C9 123.7(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C17 O4 122.1(4) . . ?
O5 C17 C18 118.4(4) . . ?
O4 C17 C18 119.3(4) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.5(4) . . ?
C21 C20 H20 119.2 . . ?
C19 C18 C17 111.5(4) . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C17 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C26 C27 H27 121.2 . . ?
C26 C27 C28 117.6(4) . . ?
C28 C27 H27 121.2 . . ?
N4 C24 C23 122.3(4) . . ?
C19 C24 N4 118.4(4) . . ?
C19 C24 C23 119.3(4) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 C24 119.8(4) . . ?
C22 C23 H23 120.1 . . ?
C23 C22 H22 119.3 . . ?
C21 C22 C23 121.3(4) . . ?
C21 C22 H22 119.3 . . ?
N4 C25 C26 121.6(4) . . ?
C30 C25 N4 122.2(4) . . ?
C30 C25 C26 116.2(4) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 C20 119.0(4) . . ?
C22 C21 H21 120.5 . . ?
N2 C11 H11A 109.4 . . ?
N2 C11 H11B 109.4 . . ?
N2 C11 C12 111.4(4) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C28 C29 C30 120.7(4) . . ?
C27 C26 Cl1 119.4(4) . . ?
C27 C26 C25 122.1(4) . . ?
C25 C26 Cl1 118.4(3) . . ?
C25 C30 Cl2 119.1(3) . . ?
C25 C30 C29 122.5(4) . . ?
C29 C30 Cl2 118.4(4) . . ?
N2 C14 H14A 109.8 . . ?
N2 C14 H14B 109.8 . . ?
N2 C14 C13 109.3(4) . . ?
H14A C14 H14B 108.3 . . ?
C13 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
N3 C12 C11 109.9(4) . . ?
N3 C12 H12A 109.7 . . ?
N3 C12 H12B 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
N3 C13 C14 109.9(4) . . ?
N3 C13 H13A 109.7 . . ?
N3 C13 H13B 109.7 . . ?
C14 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.9(4) . . ?
C29 C28 H28 119.6 . . ?

_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 1.274
_oxdiff_exptl_absorpt_empirical_full_min 0.808
####################################################################### 
# 
# 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_NOR_DIF
_database_code_depnum_ccdc_archive 'CCDC 1823916'
_audit_update_record             
;
2018-02-14 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_audit_creation_date             2017-04-13
_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         'C16 H19 F N3 O3, C13 H6 F2 O3'
_chemical_formula_sum            'C29 H25 F3 N3 O6'
_chemical_formula_weight         568.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O F'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.9178(4)
_cell_length_b                   18.4663(10)
_cell_length_c                   20.0399(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.316(5)
_cell_angle_gamma                90.00
_cell_volume                     2557.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6164
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      26.3170
_cell_measurement_theta_min      2.1850
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1180
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15195
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.03
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 119.00   1.00   12.91    --   27.17   0.00-180.00  184
  2  ω     35.00 124.00   1.00   12.91    --   27.17 178.00 150.00   89
  3  ω    -20.00  83.00   1.00   12.91    --   27.17 -99.00 -60.00  103
  4  ω    -11.00  42.00   1.00   12.91    --   27.17  57.00 -60.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0158414000
_diffrn_orient_matrix_UB_12      0.0372334000
_diffrn_orient_matrix_UB_13      0.0063836000
_diffrn_orient_matrix_UB_21      -0.0096556000
_diffrn_orient_matrix_UB_22      -0.0077981000
_diffrn_orient_matrix_UB_23      0.0343780000
_diffrn_orient_matrix_UB_31      0.1009929000
_diffrn_orient_matrix_UB_32      0.0051194000
_diffrn_orient_matrix_UB_33      0.0056641000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4481
_reflns_number_total             5143
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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         0.272
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0522
_refine_ls_restrained_S_all      1.224
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0240P)²+3.1830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1222
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: F2B(0.75) F2A(0.25)
3.a Secondary CH2 refined with riding coordinates:
 N3(H3A,H3B), C14(H14A,H14B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C21(H21), C23(H23), C1(H1), C7(H7), C20(H20), C26(H26), C28(H28)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
3.d Idealised tetrahedral OH refined as rotating group:
 O6(H6), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.3588(2) 0.66161(8) 0.35188(7) 0.0253(3) Uani 1 d . . .
F3 F 0.8371(2) 0.61766(7) 0.17905(7) 0.0280(3) Uani 1 d . . .
O5 O 0.9016(2) 1.07084(8) 0.45680(8) 0.0188(4) Uani 1 d . . .
O6 O 1.1529(2) 1.09242(9) 0.37189(8) 0.0232(4) Uani 1 d . . .
H6 H 1.0814 1.1018 0.4024 0.035 Uiso 1 calc . . GR
O3 O 0.2196(3) 0.40119(9) 0.39563(8) 0.0250(4) Uani 1 d . . .
O4 O 0.7020(3) 0.97676(9) 0.44669(9) 0.0281(4) Uani 1 d . . .
O2 O 0.1536(3) 0.28215(9) 0.45517(9) 0.0285(4) Uani 1 d . . .
H2 H 0.1642 0.3126 0.4258 0.043 Uiso 1 calc . . GR
O1 O 0.1667(3) 0.27921(9) 0.56604(10) 0.0297(4) Uani 1 d . . .
F2B F 1.2992(2) 0.79075(10) 0.24352(10) 0.0250(4) Uani 0.75 d . . .
N2 N 0.3412(3) 0.73557(10) 0.47258(9) 0.0170(4) Uani 1 d . . .
N1 N 0.2353(3) 0.50201(10) 0.57877(9) 0.0159(4) Uani 1 d . . .
N3 N 0.4180(3) 0.88686(10) 0.47776(9) 0.0172(4) Uani 1 d . . .
H3A H 0.3063 0.9048 0.4923 0.021 Uiso 1 calc . . R
H3B H 0.4990 0.9242 0.4717 0.021 Uiso 1 calc . . R
C5 C 0.2584(3) 0.54415(12) 0.52151(11) 0.0144(4) Uani 1 d . . .
C4 C 0.2561(3) 0.50921(12) 0.45877(11) 0.0156(5) Uani 1 d . . .
C10 C 0.2802(3) 0.61945(12) 0.52585(11) 0.0149(5) Uani 1 d . . .
H10 H 0.2765 0.6416 0.5674 0.018 Uiso 1 calc . . R
C19 C 1.1077(3) 1.02673(12) 0.34653(11) 0.0174(5) Uani 1 d . . .
C18 C 0.9621(3) 0.98371(12) 0.37334(11) 0.0158(5) Uani 1 d . . .
C9 C 0.3073(3) 0.66213(12) 0.46940(11) 0.0151(5) Uani 1 d . . .
C17 C 0.8463(3) 1.01103(12) 0.42991(11) 0.0168(5) Uani 1 d . . .
C24 C 0.9699(3) 0.81878(12) 0.25994(11) 0.0173(5) Uani 1 d . . .
C3 C 0.2271(3) 0.43189(12) 0.45217(12) 0.0172(5) Uani 1 d . . .
C21 C 1.1620(3) 0.93484(13) 0.26370(11) 0.0185(5) Uani 1 d . . .
H21 H 1.2279 0.9192 0.2268 0.022 Uiso 1 calc . . R
C23 C 0.9220(3) 0.91614(12) 0.34499(11) 0.0163(5) Uani 1 d . . .
H23 H 0.8277 0.8872 0.3633 0.020 Uiso 1 calc . . R
C1 C 0.2127(3) 0.43003(13) 0.57268(12) 0.0181(5) Uani 1 d . . .
H1 H 0.2000 0.4032 0.6115 0.022 Uiso 1 calc . . R
C14 C 0.2473(3) 0.78579(12) 0.42399(11) 0.0185(5) Uani 1 d . . .
H14A H 0.1258 0.8028 0.4407 0.022 Uiso 1 calc . . R
H14B H 0.2203 0.7610 0.3820 0.022 Uiso 1 calc . . R
C8 C 0.3127(3) 0.62427(13) 0.40737(11) 0.0171(5) Uani 1 d . . .
C2 C 0.2070(3) 0.39358(12) 0.51339(12) 0.0185(5) Uani 1 d . . .
C7 C 0.2856(3) 0.55217(13) 0.40185(11) 0.0180(5) Uani 1 d . . .
H7 H 0.2864 0.5305 0.3600 0.022 Uiso 1 calc . . R
C22 C 1.0191(3) 0.89056(12) 0.28994(11) 0.0168(5) Uani 1 d . . .
C11 C 0.3777(3) 0.77052(12) 0.53759(11) 0.0176(5) Uani 1 d . . .
H11A H 0.4417 0.7368 0.5683 0.021 Uiso 1 calc . . R
H11B H 0.2560 0.7848 0.5561 0.021 Uiso 1 calc . . R
C12 C 0.5046(3) 0.83687(12) 0.52890(11) 0.0183(5) Uani 1 d . . .
H12A H 0.5205 0.8621 0.5712 0.022 Uiso 1 calc . . R
H12B H 0.6315 0.8217 0.5155 0.022 Uiso 1 calc . . R
C13 C 0.3801(3) 0.84906(12) 0.41323(11) 0.0175(5) Uani 1 d . . .
H13A H 0.5009 0.8321 0.3959 0.021 Uiso 1 calc . . R
H13B H 0.3206 0.8822 0.3809 0.021 Uiso 1 calc . . R
C27 C 0.8804(4) 0.68373(13) 0.20579(11) 0.0212(5) Uani 1 d . . .
C20 C 1.2067(3) 1.00143(13) 0.29180(12) 0.0205(5) Uani 1 d . . .
H20 H 1.3035 1.0296 0.2741 0.025 Uiso 1 calc . . R
C25 C 1.1109(3) 0.77200(13) 0.23744(11) 0.0195(5) Uani 1 d . . .
C26 C 1.0715(4) 0.70439(13) 0.21009(11) 0.0218(5) Uani 1 d . . .
H26 H 1.1693 0.6745 0.1954 0.026 Uiso 1 calc . . R
C29 C 0.7788(3) 0.79405(13) 0.25342(12) 0.0218(5) Uani 1 d . . .
C6 C 0.1752(3) 0.31387(13) 0.51493(13) 0.0225(5) Uani 1 d . . .
C15 C 0.2376(4) 0.53823(13) 0.64526(11) 0.0212(5) Uani 1 d . . .
H15A H 0.1369 0.5748 0.6448 0.025 Uiso 1 calc . . R
H15B H 0.3607 0.5627 0.6526 0.025 Uiso 1 calc . . R
C28 C 0.7318(4) 0.72665(14) 0.22660(12) 0.0244(5) Uani 1 d . . .
H28 H 0.6040 0.7110 0.2228 0.029 Uiso 1 calc . . R
C16 C 0.2077(4) 0.48708(15) 0.70283(12) 0.0283(6) Uani 1 d . . .
H16A H 0.0859 0.4627 0.6962 0.042 Uiso 1 calc . . GR
H16B H 0.2080 0.5140 0.7438 0.042 Uiso 1 calc . . GR
H16C H 0.3103 0.4520 0.7051 0.042 Uiso 1 calc . . GR
F2A F 0.6348(8) 0.8326(3) 0.2698(3) 0.0291(13) Uani 0.25 d . . .


_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 C8 1.357(2) . ?
F3 C27 1.361(3) . ?
O5 C17 1.281(3) . ?
O6 H6 0.8200 . ?
O6 C19 1.347(3) . ?
O3 C3 1.266(3) . ?
O4 C17 1.240(3) . ?
O2 H2 0.8200 . ?
O2 C6 1.336(3) . ?
O1 C6 1.211(3) . ?
F2B C25 1.348(3) . ?
N2 C9 1.377(3) . ?
N2 C14 1.476(3) . ?
N2 C11 1.467(3) . ?
N1 C5 1.401(3) . ?
N1 C1 1.344(3) . ?
N1 C15 1.491(3) . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
N3 C12 1.487(3) . ?
N3 C13 1.484(3) . ?
C5 C4 1.413(3) . ?
C5 C10 1.401(3) . ?
C4 C3 1.447(3) . ?
C4 C7 1.411(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.398(3) . ?
C19 C18 1.406(3) . ?
C19 C20 1.397(3) . ?
C18 C17 1.502(3) . ?
C18 C23 1.394(3) . ?
C9 C8 1.428(3) . ?
C24 C22 1.489(3) . ?
C24 C25 1.391(3) . ?
C24 C29 1.400(3) . ?
C3 C2 1.428(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.402(3) . ?
C21 C20 1.382(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.397(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.365(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.507(3) . ?
C8 C7 1.349(3) . ?
C2 C6 1.489(3) . ?
C7 H7 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.521(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C27 C26 1.376(3) . ?
C27 C28 1.376(3) . ?
C20 H20 0.9300 . ?
C25 C26 1.386(3) . ?
C26 H26 0.9300 . ?
C29 C28 1.389(3) . ?
C29 F2A 1.279(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.512(3) . ?
C28 H28 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C19 O6 H6 109.5 . . ?
C6 O2 H2 109.5 . . ?
C9 N2 C14 121.24(19) . . ?
C9 N2 C11 119.82(18) . . ?
C11 N2 C14 111.41(18) . . ?
C5 N1 C15 119.06(18) . . ?
C1 N1 C5 119.47(19) . . ?
C1 N1 C15 121.47(19) . . ?
H3A N3 H3B 108.0 . . ?
C12 N3 H3A 109.4 . . ?
C12 N3 H3B 109.4 . . ?
C13 N3 H3A 109.4 . . ?
C13 N3 H3B 109.4 . . ?
C13 N3 C12 111.13(17) . . ?
N1 C5 C4 118.5(2) . . ?
N1 C5 C10 121.1(2) . . ?
C10 C5 C4 120.4(2) . . ?
C5 C4 C3 121.9(2) . . ?
C7 C4 C5 117.8(2) . . ?
C7 C4 C3 120.3(2) . . ?
C5 C10 H10 119.1 . . ?
C9 C10 C5 121.8(2) . . ?
C9 C10 H10 119.1 . . ?
O6 C19 C18 121.6(2) . . ?
O6 C19 C20 118.9(2) . . ?
C20 C19 C18 119.5(2) . . ?
C19 C18 C17 120.7(2) . . ?
C23 C18 C19 118.9(2) . . ?
C23 C18 C17 120.3(2) . . ?
N2 C9 C10 123.1(2) . . ?
N2 C9 C8 120.8(2) . . ?
C10 C9 C8 115.9(2) . . ?
O5 C17 C18 116.60(19) . . ?
O4 C17 O5 123.8(2) . . ?
O4 C17 C18 119.6(2) . . ?
C25 C24 C22 122.1(2) . . ?
C25 C24 C29 116.0(2) . . ?
C29 C24 C22 121.8(2) . . ?
O3 C3 C4 121.6(2) . . ?
O3 C3 C2 123.0(2) . . ?
C2 C3 C4 115.4(2) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.0(2) . . ?
C18 C23 H23 119.0 . . ?
C18 C23 C22 122.0(2) . . ?
C22 C23 H23 119.0 . . ?
N1 C1 H1 117.8 . . ?
N1 C1 C2 124.5(2) . . ?
C2 C1 H1 117.8 . . ?
N2 C14 H14A 109.9 . . ?
N2 C14 H14B 109.9 . . ?
N2 C14 C13 109.09(19) . . ?
H14A C14 H14B 108.3 . . ?
C13 C14 H14A 109.9 . . ?
C13 C14 H14B 109.9 . . ?
F1 C8 C9 118.7(2) . . ?
C7 C8 F1 118.1(2) . . ?
C7 C8 C9 123.1(2) . . ?
C3 C2 C6 121.8(2) . . ?
C1 C2 C3 120.2(2) . . ?
C1 C2 C6 117.9(2) . . ?
C4 C7 H7 119.6 . . ?
C8 C7 C4 120.9(2) . . ?
C8 C7 H7 119.6 . . ?
C21 C22 C24 121.4(2) . . ?
C23 C22 C24 120.7(2) . . ?
C23 C22 C21 117.9(2) . . ?
N2 C11 H11A 109.8 . . ?
N2 C11 H11B 109.8 . . ?
N2 C11 C12 109.40(18) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
N3 C12 C11 111.13(19) . . ?
N3 C12 H12A 109.4 . . ?
N3 C12 H12B 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
N3 C13 C14 109.10(18) . . ?
N3 C13 H13A 109.9 . . ?
N3 C13 H13B 109.9 . . ?
C14 C13 H13A 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
F3 C27 C26 117.9(2) . . ?
F3 C27 C28 118.7(2) . . ?
C26 C27 C28 123.3(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
F2B C25 C24 119.9(2) . . ?
F2B C25 C26 116.2(2) . . ?
C26 C25 C24 123.9(2) . . ?
C27 C26 C25 116.6(2) . . ?
C27 C26 H26 121.7 . . ?
C25 C26 H26 121.7 . . ?
C28 C29 C24 122.2(2) . . ?
F2A C29 C24 122.5(3) . . ?
F2A C29 C28 115.2(3) . . ?
O2 C6 C2 115.2(2) . . ?
O1 C6 O2 121.2(2) . . ?
O1 C6 C2 123.5(2) . . ?
N1 C15 H15A 108.8 . . ?
N1 C15 H15B 108.8 . . ?
N1 C15 C16 113.9(2) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C27 C28 C29 117.9(2) . . ?
C27 C28 H28 121.1 . . ?
C29 C28 H28 121.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_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 1.216
_oxdiff_exptl_absorpt_empirical_full_min 0.631
####################################################################### 
# 
# 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_NOR_MEF
_database_code_depnum_ccdc_archive 'CCDC 1823917'
_audit_update_record             
;
2018-02-14 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_audit_creation_date             2017-03-12
_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         'C16 H19 F N3 O3, C15 H14 N O2'
_chemical_formula_sum            'C31 H33 F N4 O5'
_chemical_formula_weight         560.61
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O F'
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.0624(3)
_cell_length_b                   13.6301(8)
_cell_length_c                   15.3041(7)
_cell_angle_alpha                73.354(5)
_cell_angle_beta                 77.509(4)
_cell_angle_gamma                80.518(4)
_cell_volume                     1369.72(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4530
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      26.3460
_cell_measurement_theta_min      2.3480
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83381
_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_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10966
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.82
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -123.00 -55.00   1.00   45.92    --  -27.14 178.00-180.00   68
  2  ω   -123.00 -55.00   1.00   45.92    --  -27.14 178.00   0.00   68
  3  ω     58.00 112.00   1.00   45.92    --   28.55 150.00-156.00   54
  4  ω    -48.00  67.00   1.00   45.92    --   28.55 -57.00 -30.00  115
  5  ω    -25.00  58.00   1.00   45.92    --   28.55 -57.00 150.00   83
  6  ω    -48.00 117.00   1.00   45.92    --   28.55  19.00 -30.00  165
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0091054000
_diffrn_orient_matrix_UB_12      -0.0121821000
_diffrn_orient_matrix_UB_13      0.0488920000
_diffrn_orient_matrix_UB_21      0.0406110000
_diffrn_orient_matrix_UB_22      -0.0513248000
_diffrn_orient_matrix_UB_23      0.0005946000
_diffrn_orient_matrix_UB_31      0.0947570000
_diffrn_orient_matrix_UB_32      0.0142679000
_diffrn_orient_matrix_UB_33      -0.0051658000
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4541
_reflns_number_total             5594
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5594
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0315P)²+1.0243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1164
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 N3(H3A,H3B), C14(H14A,H14B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B),
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), C7(H7), C1(H1), C10(H10), C26(H26), C27(H27), C25(H25), C19(H19),
 C22(H22), C21(H21), C20(H20)
2.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F -0.40028(17) 0.83964(9) 0.97370(8) 0.0252(3) Uani 1 d . . .
O5 O 0.42537(19) 0.91562(11) 0.42453(10) 0.0246(3) Uani 1 d . . .
O3 O -0.2739(2) 0.47563(11) 1.15481(9) 0.0234(3) Uani 1 d . . .
O2 O -0.1708(2) 0.28440(11) 1.19671(9) 0.0255(3) Uani 1 d . . .
H2 H -0.2073 0.3439 1.1995 0.038 Uiso 1 calc . . GR
O1 O -0.0957(2) 0.19874(11) 1.08795(10) 0.0282(3) Uani 1 d . . .
O4 O 0.1997(2) 0.85381(12) 0.54431(11) 0.0342(4) Uani 1 d . . .
N1 N -0.2354(2) 0.46606(12) 0.88589(10) 0.0168(3) Uani 1 d . . .
N3 N -0.1460(2) 0.92825(12) 0.61941(11) 0.0172(3) Uani 1 d . . .
H3A H -0.0328 0.9264 0.5791 0.021 Uiso 1 calc . . R
H3B H -0.2222 0.9854 0.5960 0.021 Uiso 1 calc . . R
N2 N -0.3909(2) 0.83951(12) 0.79140(11) 0.0182(3) Uani 1 d . . .
N4 N 0.7498(2) 0.79757(13) 0.38910(11) 0.0223(4) Uani 1 d . . .
H4 H 0.6782 0.8557 0.3791 0.027 Uiso 1 calc . . R
C5 C -0.2803(2) 0.56128(14) 0.90684(12) 0.0153(4) Uani 1 d . . .
C7 C -0.3287(3) 0.66164(15) 1.01851(13) 0.0178(4) Uani 1 d . . .
H7 H -0.3361 0.6658 1.0788 0.021 Uiso 1 calc . . R
C4 C -0.2884(2) 0.56505(15) 0.99865(12) 0.0161(4) Uani 1 d . . .
C3 C -0.2559(2) 0.47254(15) 1.07145(13) 0.0172(4) Uani 1 d . . .
C23 C 0.6675(3) 0.71921(14) 0.45951(12) 0.0160(4) Uani 1 d . . .
C1 C -0.1949(3) 0.38070(15) 0.95203(13) 0.0179(4) Uani 1 d . . .
H1 H -0.1600 0.3188 0.9354 0.021 Uiso 1 calc . . R
C2 C -0.2019(3) 0.37906(15) 1.04273(13) 0.0176(4) Uani 1 d . . .
C9 C -0.3506(2) 0.74857(14) 0.85705(12) 0.0163(4) Uani 1 d . . .
C29 C 0.9506(3) 0.84906(14) 0.23704(13) 0.0175(4) Uani 1 d . . .
C17 C 0.3601(3) 0.84365(15) 0.49270(13) 0.0183(4) Uani 1 d . . .
C18 C 0.4807(3) 0.74032(15) 0.51187(12) 0.0165(4) Uani 1 d . . .
C10 C -0.3142(3) 0.65240(14) 0.83801(12) 0.0163(4) Uani 1 d . . .
H10 H -0.3122 0.6485 0.7781 0.020 Uiso 1 calc . . R
C26 C 1.2836(3) 0.75052(15) 0.31056(14) 0.0198(4) Uani 1 d . . .
H26 H 1.3944 0.7171 0.3345 0.024 Uiso 1 calc . . R
C8 C -0.3568(3) 0.74871(15) 0.95067(13) 0.0184(4) Uani 1 d . . .
C27 C 1.2997(3) 0.80294(15) 0.21750(13) 0.0192(4) Uani 1 d . . .
H27 H 1.4217 0.8039 0.1794 0.023 Uiso 1 calc . . R
C14 C -0.2924(3) 0.93060(15) 0.78102(13) 0.0201(4) Uani 1 d . . .
H14A H -0.2618 0.9290 0.8402 0.024 Uiso 1 calc . . R
H14B H -0.3797 0.9925 0.7624 0.024 Uiso 1 calc . . R
C28 C 1.1361(3) 0.85398(14) 0.18039(13) 0.0182(4) Uani 1 d . . .
C12 C -0.2442(3) 0.83589(15) 0.62955(13) 0.0194(4) Uani 1 d . . .
H12A H -0.1576 0.7738 0.6485 0.023 Uiso 1 calc . . R
H12B H -0.2762 0.8373 0.5707 0.023 Uiso 1 calc . . R
C25 C 1.1020(3) 0.74797(15) 0.36799(13) 0.0189(4) Uani 1 d . . .
H25 H 1.0918 0.7147 0.4308 0.023 Uiso 1 calc . . R
C19 C 0.3991(3) 0.66095(15) 0.58352(13) 0.0191(4) Uani 1 d . . .
H19 H 0.2781 0.6754 0.6187 0.023 Uiso 1 calc . . R
C22 C 0.7588(3) 0.61776(15) 0.48023(13) 0.0190(4) Uani 1 d . . .
H22 H 0.8803 0.6020 0.4461 0.023 Uiso 1 calc . . R
C21 C 0.6718(3) 0.54068(15) 0.55031(14) 0.0215(4) Uani 1 d . . .
H21 H 0.7344 0.4739 0.5618 0.026 Uiso 1 calc . . R
C24 C 0.9347(3) 0.79534(14) 0.33149(13) 0.0172(4) Uani 1 d . . .
C6 C -0.1517(3) 0.27901(16) 1.10925(13) 0.0210(4) Uani 1 d . . .
C13 C -0.1060(3) 0.93381(14) 0.70941(13) 0.0182(4) Uani 1 d . . .
H13A H -0.0500 0.9971 0.7006 0.022 Uiso 1 calc . . R
H13B H -0.0122 0.8764 0.7315 0.022 Uiso 1 calc . . R
C15 C -0.2207(3) 0.45823(15) 0.78984(13) 0.0207(4) Uani 1 d . . .
H15A H -0.3276 0.5023 0.7631 0.025 Uiso 1 calc . . R
H15B H -0.2330 0.3879 0.7915 0.025 Uiso 1 calc . . R
C11 C -0.4297(3) 0.83610(15) 0.70216(13) 0.0190(4) Uani 1 d . . .
H11A H -0.5199 0.8954 0.6800 0.023 Uiso 1 calc . . R
H11B H -0.4912 0.7746 0.7107 0.023 Uiso 1 calc . . R
C20 C 0.4918(3) 0.56198(15) 0.60374(13) 0.0219(4) Uani 1 d . . .
H20 H 0.4352 0.5106 0.6521 0.026 Uiso 1 calc . . R
C30 C 1.1586(3) 0.91660(16) 0.08028(13) 0.0244(4) Uani 1 d . . .
H30A H 1.1028 0.8840 0.0455 0.037 Uiso 1 calc . . GR
H30B H 1.2946 0.9209 0.0548 0.037 Uiso 1 calc . . GR
H30C H 1.0927 0.9847 0.0771 0.037 Uiso 1 calc . . GR
C31 C 0.7732(3) 0.90512(17) 0.19675(15) 0.0262(5) Uani 1 d . . .
H31A H 0.7633 0.9769 0.1945 0.039 Uiso 1 calc . . GR
H31B H 0.6582 0.8765 0.2350 0.039 Uiso 1 calc . . GR
H31C H 0.7852 0.8976 0.1352 0.039 Uiso 1 calc . . GR
C16 C -0.0288(3) 0.48932(18) 0.72899(14) 0.0282(5) Uani 1 d . . .
H16A H -0.0283 0.4872 0.6668 0.042 Uiso 1 calc . . GR
H16B H 0.0769 0.4425 0.7525 0.042 Uiso 1 calc . . GR
H16C H -0.0136 0.5579 0.7292 0.042 Uiso 1 calc . . GR


_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 C8 1.354(2) . ?
O5 C17 1.272(2) . ?
O3 C3 1.267(2) . ?
O2 H2 0.8200 . ?
O2 C6 1.338(2) . ?
O1 C6 1.211(2) . ?
O4 C17 1.245(2) . ?
N1 C5 1.395(2) . ?
N1 C1 1.342(2) . ?
N1 C15 1.484(2) . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
N3 C12 1.490(2) . ?
N3 C13 1.489(2) . ?
N2 C9 1.386(2) . ?
N2 C14 1.474(2) . ?
N2 C11 1.465(2) . ?
N4 H4 0.8600 . ?
N4 C23 1.383(2) . ?
N4 C24 1.410(2) . ?
C5 C4 1.409(3) . ?
C5 C10 1.404(3) . ?
C7 H7 0.9300 . ?
C7 C4 1.405(3) . ?
C7 C8 1.353(3) . ?
C4 C3 1.447(3) . ?
C3 C2 1.432(3) . ?
C23 C18 1.420(3) . ?
C23 C22 1.404(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.372(3) . ?
C2 C6 1.491(3) . ?
C9 C10 1.395(3) . ?
C9 C8 1.425(3) . ?
C29 C28 1.406(3) . ?
C29 C24 1.410(3) . ?
C29 C31 1.511(3) . ?
C17 C18 1.507(3) . ?
C18 C19 1.399(3) . ?
C10 H10 0.9300 . ?
C26 H26 0.9300 . ?
C26 C27 1.388(3) . ?
C26 C25 1.388(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.390(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.518(3) . ?
C28 C30 1.514(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.524(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.397(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.383(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.390(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.517(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C20 H20 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 H2 109.5 . . ?
C5 N1 C15 120.89(15) . . ?
C1 N1 C5 119.94(16) . . ?
C1 N1 C15 119.08(16) . . ?
H3A N3 H3B 107.9 . . ?
C12 N3 H3A 109.2 . . ?
C12 N3 H3B 109.2 . . ?
C13 N3 H3A 109.2 . . ?
C13 N3 H3B 109.2 . . ?
C13 N3 C12 112.11(14) . . ?
C9 N2 C14 120.25(16) . . ?
C9 N2 C11 119.86(16) . . ?
C11 N2 C14 110.96(15) . . ?
C23 N4 H4 115.5 . . ?
C23 N4 C24 129.01(16) . . ?
C24 N4 H4 115.5 . . ?
N1 C5 C4 118.79(16) . . ?
N1 C5 C10 121.11(16) . . ?
C10 C5 C4 120.09(17) . . ?
C4 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C8 C7 C4 120.57(17) . . ?
C5 C4 C3 121.53(17) . . ?
C7 C4 C5 118.35(17) . . ?
C7 C4 C3 120.12(17) . . ?
O3 C3 C4 121.31(18) . . ?
O3 C3 C2 122.97(17) . . ?
C2 C3 C4 115.71(16) . . ?
N4 C23 C18 119.35(17) . . ?
N4 C23 C22 122.72(17) . . ?
C22 C23 C18 117.91(17) . . ?
N1 C1 H1 118.0 . . ?
N1 C1 C2 124.06(18) . . ?
C2 C1 H1 118.0 . . ?
C3 C2 C6 121.51(17) . . ?
C1 C2 C3 119.78(17) . . ?
C1 C2 C6 118.71(18) . . ?
N2 C9 C10 123.11(17) . . ?
N2 C9 C8 120.58(17) . . ?
C10 C9 C8 116.21(17) . . ?
C28 C29 C24 119.22(17) . . ?
C28 C29 C31 119.51(17) . . ?
C24 C29 C31 121.22(16) . . ?
O5 C17 C18 118.84(16) . . ?
O4 C17 O5 123.22(18) . . ?
O4 C17 C18 117.94(17) . . ?
C23 C18 C17 123.55(16) . . ?
C19 C18 C23 119.07(17) . . ?
C19 C18 C17 117.35(16) . . ?
C5 C10 H10 119.1 . . ?
C9 C10 C5 121.75(17) . . ?
C9 C10 H10 119.1 . . ?
C27 C26 H26 120.0 . . ?
C27 C26 C25 119.99(17) . . ?
C25 C26 H26 120.0 . . ?
F1 C8 C9 118.56(16) . . ?
C7 C8 F1 118.36(17) . . ?
C7 C8 C9 123.02(18) . . ?
C26 C27 H27 119.5 . . ?
C26 C27 C28 120.99(17) . . ?
C28 C27 H27 119.5 . . ?
N2 C14 H14A 109.3 . . ?
N2 C14 H14B 109.3 . . ?
N2 C14 C13 111.40(15) . . ?
H14A C14 H14B 108.0 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C29 C28 C30 120.31(17) . . ?
C27 C28 C29 119.58(17) . . ?
C27 C28 C30 120.08(17) . . ?
N3 C12 H12A 109.9 . . ?
N3 C12 H12B 109.9 . . ?
N3 C12 C11 108.96(15) . . ?
H12A C12 H12B 108.3 . . ?
C11 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
C26 C25 H25 120.0 . . ?
C26 C25 C24 120.02(17) . . ?
C24 C25 H25 120.0 . . ?
C18 C19 H19 118.9 . . ?
C20 C19 C18 122.25(18) . . ?
C20 C19 H19 118.9 . . ?
C23 C22 H22 119.3 . . ?
C21 C22 C23 121.42(17) . . ?
C21 C22 H22 119.3 . . ?
C22 C21 H21 119.6 . . ?
C22 C21 C20 120.74(18) . . ?
C20 C21 H21 119.6 . . ?
N4 C24 C29 118.65(16) . . ?
C25 C24 N4 121.05(17) . . ?
C25 C24 C29 120.11(16) . . ?
O2 C6 C2 114.29(17) . . ?
O1 C6 O2 121.38(18) . . ?
O1 C6 C2 124.33(18) . . ?
N3 C13 C14 110.65(15) . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
N1 C15 H15A 109.2 . . ?
N1 C15 H15B 109.2 . . ?
N1 C15 C16 112.08(15) . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
N2 C11 C12 112.21(15) . . ?
N2 C11 H11A 109.2 . . ?
N2 C11 H11B 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C19 C20 C21 118.56(18) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_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 1.213
_oxdiff_exptl_absorpt_empirical_full_min 0.597
####################################################################### 
# 
# 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_NOR_IND_H2O
_database_code_depnum_ccdc_archive 'CCDC 1823918'
_audit_update_record             
;
2018-02-14 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_audit_creation_date             2017-04-06
_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 H15 Cl N O4, C16 H19 F N3 O3, H2 O'
_chemical_formula_sum            'C35 H36 Cl F N4 O8'
_chemical_formula_weight         695.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O F Cl '
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   18.5334(7)
_cell_length_b                   6.7235(3)
_cell_length_c                   25.4164(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.407(4)
_cell_angle_gamma                90.00
_cell_volume                     3166.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4161
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.3280
_cell_measurement_theta_min      2.1790
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10579
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.60
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9889
_diffrn_measured_fraction_theta_max 0.9891
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00 117.00   1.00  106.41    --   28.47   0.00-120.00  180
  2  ω     10.00  73.00   1.00  106.41    --   28.47 -77.00  60.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0321469000
_diffrn_orient_matrix_UB_12      0.0419780000
_diffrn_orient_matrix_UB_13      0.0096532000
_diffrn_orient_matrix_UB_21      -0.0190887000
_diffrn_orient_matrix_UB_22      -0.0320098000
_diffrn_orient_matrix_UB_23      -0.0230546000
_diffrn_orient_matrix_UB_31      -0.0081382000
_diffrn_orient_matrix_UB_32      -0.0913415000
_diffrn_orient_matrix_UB_33      0.0124681000
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5021
_reflns_number_total             6416
_reflns_odcompleteness_completeness 98.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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         0.311
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         6416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1672
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O8(H8A,H8B)
2.b Secondary CH2 refined with riding coordinates:
 N3(H3A,H3B), C14(H14A,H14B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B),
 C27(H27A,H27B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C31(H31), C24(H24), C1(H1), C32(H32), C21(H21), C35(H35),
 C22(H22), C34(H34)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C16(H16A,H16B,H16C), C26(H26A,H26B,H26C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.14244(3) 0.43081(9) 0.68594(2) 0.02892(18) Uani 1 d . . .
F1 F 0.81180(7) 1.2224(2) 0.39316(5) 0.0252(3) Uani 1 d . . .
O3 O 1.08004(9) 1.2629(2) 0.41649(7) 0.0232(4) Uani 1 d . . .
O5 O 0.51355(9) 0.6126(2) 0.55870(7) 0.0250(4) Uani 1 d . . .
O4 O 0.57581(10) 0.8622(3) 0.52581(7) 0.0278(4) Uani 1 d . . .
O7 O 0.47167(10) 0.3231(3) 0.79289(7) 0.0312(4) Uani 1 d . . .
O2 O 1.20448(9) 1.3088(3) 0.45677(7) 0.0301(4) Uani 1 d . . .
H2 H 1.1701 1.2975 0.4348 0.045 Uiso 1 calc . . GR
O1 O 1.21827(9) 1.3398(3) 0.54321(7) 0.0313(4) Uani 1 d . . .
O6 O 0.77541(10) 0.1815(3) 0.66687(7) 0.0333(5) Uani 1 d . . .
N1 N 0.99945(10) 1.2337(3) 0.56509(7) 0.0193(4) Uani 1 d . . .
O8 O 0.46755(13) 0.2291(3) 0.58088(8) 0.0411(5) Uani 1 d . . .
H8A H 0.4859 0.3450 0.5821 0.062 Uiso 1 d . . G
H8B H 0.4492 0.2085 0.5504 0.062 Uiso 1 d . . G
N4 N 0.50790(10) 0.4726(3) 0.71774(7) 0.0229(4) Uani 1 d . . .
N3 N 0.60236(10) 1.2393(3) 0.49641(8) 0.0206(4) Uani 1 d . . .
H3A H 0.5874 1.1245 0.5125 0.025 Uiso 1 calc . . R
H3B H 0.5623 1.3165 0.4894 0.025 Uiso 1 calc . . R
N2 N 0.75428(10) 1.1867(3) 0.49224(8) 0.0214(4) Uani 1 d . . .
C7 C 0.92932(12) 1.2361(3) 0.42763(9) 0.0177(5) Uani 1 d . . .
H7 H 0.9465 1.2448 0.3928 0.021 Uiso 1 calc . . R
C10 C 0.87639(12) 1.2063(3) 0.52908(9) 0.0180(5) Uani 1 d . . .
H10 H 0.8588 1.1951 0.5638 0.022 Uiso 1 calc . . R
C28 C 0.55732(12) 0.7532(3) 0.56346(9) 0.0185(5) Uani 1 d . . .
C4 C 0.97818(12) 1.2437(3) 0.47089(9) 0.0176(5) Uani 1 d . . .
C9 C 0.82751(12) 1.1988(3) 0.48631(9) 0.0179(5) Uani 1 d . . .
C8 C 0.85786(12) 1.2165(3) 0.43580(9) 0.0182(5) Uani 1 d . . .
C5 C 0.95047(12) 1.2300(3) 0.52204(9) 0.0174(5) Uani 1 d . . .
C3 C 1.05467(12) 1.2635(3) 0.46227(9) 0.0190(5) Uani 1 d . . .
C19 C 0.61455(13) 0.4849(3) 0.67582(9) 0.0217(5) Uani 1 d . . .
C31 C 0.32516(13) 0.4396(3) 0.77104(9) 0.0213(5) Uani 1 d . . .
H31 H 0.3391 0.4503 0.8071 0.026 Uiso 1 calc . . R
C2 C 1.09968(12) 1.2837(3) 0.50842(10) 0.0204(5) Uani 1 d . . .
C14 C 0.70564(12) 1.0701(4) 0.45782(10) 0.0226(5) Uani 1 d . . .
H14A H 0.6935 0.9431 0.4752 0.027 Uiso 1 calc . . R
H14B H 0.7299 1.0390 0.4245 0.027 Uiso 1 calc . . R
C30 C 0.37799(13) 0.4186(3) 0.73333(9) 0.0215(5) Uani 1 d . . .
C24 C 0.68313(13) 0.4180(4) 0.66249(9) 0.0238(5) Uani 1 d . . .
H24 H 0.7120 0.4934 0.6394 0.029 Uiso 1 calc . . R
C20 C 0.57444(12) 0.3751(4) 0.71208(9) 0.0221(5) Uani 1 d . . .
C11 C 0.72131(13) 1.2307(4) 0.54255(9) 0.0229(5) Uani 1 d . . .
H11A H 0.7553 1.3083 0.5651 0.027 Uiso 1 calc . . R
H11B H 0.7101 1.1052 0.5610 0.027 Uiso 1 calc . . R
C1 C 1.07012(13) 1.2629(3) 0.55724(10) 0.0211(5) Uani 1 d . . .
H1 H 1.1016 1.2695 0.5873 0.025 Uiso 1 calc . . R
C18 C 0.57114(13) 0.6535(4) 0.65963(9) 0.0226(5) Uani 1 d . . .
C17 C 0.50803(13) 0.6446(4) 0.68528(9) 0.0222(5) Uani 1 d . . .
C29 C 0.45428(13) 0.4039(4) 0.75141(9) 0.0237(5) Uani 1 d . . .
C12 C 0.65266(12) 1.3489(4) 0.53273(10) 0.0230(5) Uani 1 d . . .
H12A H 0.6288 1.3732 0.5666 0.028 Uiso 1 calc . . R
H12B H 0.6647 1.4794 0.5172 0.028 Uiso 1 calc . . R
C32 C 0.25291(13) 0.4451(3) 0.75666(10) 0.0227(5) Uani 1 d . . .
H32 H 0.2171 0.4631 0.7824 0.027 Uiso 1 calc . . R
C33 C 0.23357(12) 0.4238(3) 0.70371(10) 0.0219(5) Uani 1 d . . .
C21 C 0.59981(13) 0.1989(4) 0.73340(10) 0.0256(5) Uani 1 d . . .
H21 H 0.5719 0.1262 0.7577 0.031 Uiso 1 calc . . R
C23 C 0.70838(13) 0.2407(4) 0.68335(10) 0.0257(5) Uani 1 d . . .
C15 C 0.97758(14) 1.1798(4) 0.61932(9) 0.0244(5) Uani 1 d . . .
H15A H 1.0199 1.1230 0.6385 0.029 Uiso 1 calc . . R
H15B H 0.9402 1.0750 0.6168 0.029 Uiso 1 calc . . R
C27 C 0.59023(13) 0.8008(4) 0.61788(9) 0.0231(5) Uani 1 d . . .
H27A H 0.6434 0.8057 0.6153 0.028 Uiso 1 calc . . R
H27B H 0.5737 0.9343 0.6287 0.028 Uiso 1 calc . . R
C13 C 0.63704(13) 1.1879(4) 0.44615(9) 0.0238(5) Uani 1 d . . .
H13A H 0.6488 1.3109 0.4268 0.029 Uiso 1 calc . . R
H13B H 0.6035 1.1078 0.4239 0.029 Uiso 1 calc . . R
C35 C 0.35700(13) 0.3938(4) 0.68066(10) 0.0263(5) Uani 1 d . . .
H35 H 0.3927 0.3749 0.6549 0.032 Uiso 1 calc . . R
C22 C 0.66707(14) 0.1302(4) 0.71860(10) 0.0266(5) Uani 1 d . . .
H22 H 0.6852 0.0081 0.7324 0.032 Uiso 1 calc . . R
C34 C 0.28458(13) 0.3965(4) 0.66550(10) 0.0254(5) Uani 1 d . . .
H34 H 0.2703 0.3800 0.6296 0.031 Uiso 1 calc . . R
C6 C 1.17872(13) 1.3130(3) 0.50536(10) 0.0237(5) Uani 1 d . . .
C25 C 0.44948(15) 0.7975(4) 0.68643(10) 0.0300(6) Uani 1 d . . .
H25A H 0.4063 0.7464 0.6679 0.045 Uiso 1 calc . . GR
H25B H 0.4658 0.9192 0.6691 0.045 Uiso 1 calc . . GR
H25C H 0.4380 0.8272 0.7230 0.045 Uiso 1 calc . . GR
C16 C 0.94863(14) 1.3509(4) 0.65096(10) 0.0286(6) Uani 1 d . . .
H16A H 0.9051 1.4039 0.6334 0.043 Uiso 1 calc . . GR
H16B H 0.9853 1.4557 0.6539 0.043 Uiso 1 calc . . GR
H16C H 0.9367 1.3040 0.6862 0.043 Uiso 1 calc . . GR
C26 C 0.80086(15) -0.0064(4) 0.68434(11) 0.0366(7) Uani 1 d . . .
H26A H 0.8477 -0.0338 0.6688 0.055 Uiso 1 calc . . GR
H26B H 0.7663 -0.1097 0.6735 0.055 Uiso 1 calc . . GR
H26C H 0.8062 -0.0056 0.7228 0.055 Uiso 1 calc . . GR


_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 C33 1.738(2) . ?
F1 C8 1.364(2) . ?
O3 C3 1.266(3) . ?
O5 C28 1.250(3) . ?
O4 C28 1.259(3) . ?
O7 C29 1.222(3) . ?
O2 H2 0.8400 . ?
O2 C6 1.335(3) . ?
O1 C6 1.208(3) . ?
O6 C23 1.379(3) . ?
O6 C26 1.416(3) . ?
N1 C5 1.405(3) . ?
N1 C1 1.344(3) . ?
N1 C15 1.491(3) . ?
O8 H8A 0.8502 . ?
O8 H8B 0.8498 . ?
N4 C20 1.407(3) . ?
N4 C17 1.420(3) . ?
N4 C29 1.405(3) . ?
N3 H3A 0.9200 . ?
N3 H3B 0.9200 . ?
N3 C12 1.491(3) . ?
N3 C13 1.485(3) . ?
N2 C9 1.372(3) . ?
N2 C14 1.468(3) . ?
N2 C11 1.461(3) . ?
C7 H7 0.9500 . ?
C7 C4 1.408(3) . ?
C7 C8 1.352(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.399(3) . ?
C10 C5 1.398(3) . ?
C28 C27 1.532(3) . ?
C4 C5 1.413(3) . ?
C4 C3 1.446(3) . ?
C9 C8 1.419(3) . ?
C3 C2 1.429(3) . ?
C19 C24 1.398(3) . ?
C19 C20 1.407(3) . ?
C19 C18 1.444(3) . ?
C31 H31 0.9500 . ?
C31 C30 1.394(3) . ?
C31 C32 1.380(3) . ?
C2 C1 1.376(3) . ?
C2 C6 1.482(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.521(3) . ?
C30 C29 1.479(3) . ?
C30 C35 1.395(3) . ?
C24 H24 0.9500 . ?
C24 C23 1.382(4) . ?
C20 C21 1.380(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.516(3) . ?
C1 H1 0.9500 . ?
C18 C17 1.354(3) . ?
C18 C27 1.500(3) . ?
C17 C25 1.496(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C32 H32 0.9500 . ?
C32 C33 1.392(3) . ?
C33 C34 1.384(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(4) . ?
C23 C22 1.405(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.509(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C35 H35 0.9500 . ?
C35 C34 1.387(3) . ?
C22 H22 0.9500 . ?
C34 H34 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 H2 109.5 . . ?
C23 O6 C26 117.2(2) . . ?
C5 N1 C15 122.05(19) . . ?
C1 N1 C5 120.0(2) . . ?
C1 N1 C15 117.4(2) . . ?
H8A O8 H8B 109.5 . . ?
C20 N4 C17 107.81(19) . . ?
C29 N4 C20 122.9(2) . . ?
C29 N4 C17 129.2(2) . . ?
H3A N3 H3B 107.9 . . ?
C12 N3 H3A 109.3 . . ?
C12 N3 H3B 109.3 . . ?
C13 N3 H3A 109.3 . . ?
C13 N3 H3B 109.3 . . ?
C13 N3 C12 111.75(18) . . ?
C9 N2 C14 124.14(19) . . ?
C9 N2 C11 121.35(19) . . ?
C11 N2 C14 111.47(18) . . ?
C4 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C8 C7 C4 119.8(2) . . ?
C9 C10 H10 119.2 . . ?
C5 C10 H10 119.2 . . ?
C5 C10 C9 121.6(2) . . ?
O5 C28 O4 123.7(2) . . ?
O5 C28 C27 119.2(2) . . ?
O4 C28 C27 117.1(2) . . ?
C7 C4 C5 118.4(2) . . ?
C7 C4 C3 119.9(2) . . ?
C5 C4 C3 121.7(2) . . ?
N2 C9 C10 122.7(2) . . ?
N2 C9 C8 121.3(2) . . ?
C10 C9 C8 115.9(2) . . ?
F1 C8 C9 117.84(19) . . ?
C7 C8 F1 118.1(2) . . ?
C7 C8 C9 124.0(2) . . ?
N1 C5 C4 118.2(2) . . ?
C10 C5 N1 121.4(2) . . ?
C10 C5 C4 120.4(2) . . ?
O3 C3 C4 121.8(2) . . ?
O3 C3 C2 122.2(2) . . ?
C2 C3 C4 116.0(2) . . ?
C24 C19 C20 119.2(2) . . ?
C24 C19 C18 133.4(2) . . ?
C20 C19 C18 107.4(2) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C32 C31 C30 120.9(2) . . ?
C3 C2 C6 121.8(2) . . ?
C1 C2 C3 119.6(2) . . ?
C1 C2 C6 118.5(2) . . ?
N2 C14 H14A 109.7 . . ?
N2 C14 H14B 109.7 . . ?
N2 C14 C13 109.66(19) . . ?
H14A C14 H14B 108.2 . . ?
C13 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
C31 C30 C29 118.4(2) . . ?
C31 C30 C35 119.2(2) . . ?
C35 C30 C29 122.1(2) . . ?
C19 C24 H24 120.5 . . ?
C23 C24 C19 119.1(2) . . ?
C23 C24 H24 120.5 . . ?
N4 C20 C19 107.5(2) . . ?
C21 C20 N4 130.6(2) . . ?
C21 C20 C19 121.8(2) . . ?
N2 C11 H11A 109.8 . . ?
N2 C11 H11B 109.8 . . ?
N2 C11 C12 109.23(19) . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
N1 C1 C2 124.0(2) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C19 C18 C27 125.5(2) . . ?
C17 C18 C19 108.0(2) . . ?
C17 C18 C27 126.2(2) . . ?
N4 C17 C25 122.5(2) . . ?
C18 C17 N4 109.2(2) . . ?
C18 C17 C25 127.9(2) . . ?
O7 C29 N4 119.7(2) . . ?
O7 C29 C30 121.8(2) . . ?
N4 C29 C30 118.3(2) . . ?
N3 C12 C11 110.64(19) . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C31 C32 H32 120.7 . . ?
C31 C32 C33 118.6(2) . . ?
C33 C32 H32 120.7 . . ?
C32 C33 Cl1 118.29(18) . . ?
C34 C33 Cl1 119.83(19) . . ?
C34 C33 C32 121.9(2) . . ?
C20 C21 H21 120.7 . . ?
C20 C21 C22 118.6(2) . . ?
C22 C21 H21 120.7 . . ?
O6 C23 C24 115.6(2) . . ?
O6 C23 C22 123.4(2) . . ?
C24 C23 C22 121.1(2) . . ?
N1 C15 H15A 108.6 . . ?
N1 C15 H15B 108.6 . . ?
N1 C15 C16 114.6(2) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C28 C27 H27A 108.8 . . ?
C28 C27 H27B 108.8 . . ?
C18 C27 C28 113.93(19) . . ?
C18 C27 H27A 108.8 . . ?
C18 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
N3 C13 C14 109.33(19) . . ?
N3 C13 H13A 109.8 . . ?
N3 C13 H13B 109.8 . . ?
C14 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
C30 C35 H35 119.7 . . ?
C34 C35 C30 120.7(2) . . ?
C34 C35 H35 119.7 . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C33 C34 C35 118.7(2) . . ?
C33 C34 H34 120.7 . . ?
C35 C34 H34 120.7 . . ?
O2 C6 C2 115.0(2) . . ?
O1 C6 O2 121.0(2) . . ?
O1 C6 C2 124.0(2) . . ?
C17 C25 H25A 109.5 . . ?
C17 C25 H25B 109.5 . . ?
C17 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C26 H26A 109.5 . . ?
O6 C26 H26B 109.5 . . ?
O6 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_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 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.826
