# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_zc-3
_database_code_depnum_ccdc_archive 'CCDC 2038579'
_audit_update_record             
;
2020-10-15 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2020-03-27
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H29 F N2 O3'
_chemical_formula_sum            'C29 H29 F N2 O3'
_chemical_formula_weight         472.54
_chemical_absolute_configuration ad
_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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.32490(16)
_cell_length_b                   10.11966(12)
_cell_length_c                   11.47015(15)
_cell_angle_alpha                90
_cell_angle_beta                 106.0020(14)
_cell_angle_gamma                90
_cell_volume                     1263.59(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6888
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3460
_cell_measurement_theta_min      3.9860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61642
_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    1.242
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_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  0.0245
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8662
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.716
_diffrn_reflns_theta_min         4.009
_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 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00  -5.00   1.00    1.00    --  -40.98 124.00 -30.00   80
  2  ω   -112.00  -6.00   1.00    1.00    --  -40.98 -19.00-120.00  106
  3  ω     44.00  88.00   1.00    1.00    --   40.98-124.00-120.00   44
  4  ω     35.00 134.00   1.00    1.50    --  106.95 -61.00-180.00   99
  5  ω     64.00 121.00   1.00    1.50    --  106.95-124.00-150.00   57
  6  ω     54.00 130.00   1.00    1.50    --  106.95 -45.00 -90.00   76
  7  ω     82.00 174.00   1.00    1.50    --  106.95  45.00   0.00   92
  8  ω    153.00 178.00   1.00    1.50    --  106.95 124.00  30.00   25
  9  ω     94.00 177.00   1.00    1.50    --  106.95  61.00-120.00   83
 10  ω    145.00 172.00   1.00    1.50    --  106.95 124.00-180.00   27
 11  ω    100.00 130.00   1.00    1.50    --  106.95 124.00-180.00   30
 12  ω     90.00 176.00   1.00    1.50    --  106.95  45.00 -60.00   86
 13  ω     56.00 127.00   1.00    1.50    --  106.95 -45.00  60.00   71
 14  ω     29.00  91.00   1.00    1.50    --  106.95 -94.00  90.00   62
 15  ω     28.00 109.00   1.00    1.50    --  106.95 -94.00 -30.00   81
 16  ω     23.00  53.00   1.00    1.00    --   40.98-124.00 150.00   30
 17  ω   -114.00 -34.00   1.00    1.00    --  -40.98 -37.00-180.00   80
;
_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      0.0539667000
_diffrn_orient_matrix_UB_12      -0.0436533000
_diffrn_orient_matrix_UB_13      0.1326146000
_diffrn_orient_matrix_UB_21      -0.1232179000
_diffrn_orient_matrix_UB_22      0.0312684000
_diffrn_orient_matrix_UB_23      0.0263444000
_diffrn_orient_matrix_UB_31      -0.0439243000
_diffrn_orient_matrix_UB_32      -0.1425201000
_diffrn_orient_matrix_UB_33      -0.0350617000
_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         0.642
_reflns_Friedel_fraction_full    0.750
_reflns_Friedel_fraction_max     0.715
_reflns_number_gt                4295
_reflns_number_total             4383
_reflns_odcompleteness_completeness 100.00
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1644 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_coef       0.0050(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4383
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.039
_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)+(0.0405P)²+0.0948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0709
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C)
;
_atom_sites_solution_hydrogens   mixed
_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
F1 F -0.05856(10) 0.44148(14) 0.35673(11) 0.0410(3) Uani 1 1 d . . . . .
O1 O 0.34943(11) 0.43591(13) 0.26286(10) 0.0247(3) Uani 1 1 d . . . . .
O2 O 0.53363(11) 0.53102(13) 0.26820(10) 0.0263(3) Uani 1 1 d . . . . .
O3 O 0.40308(11) 0.28845(12) 0.52156(11) 0.0257(3) Uani 1 1 d . . . . .
N1 N 0.20661(13) 0.37107(15) 0.45281(12) 0.0230(3) Uani 1 1 d . . . . .
N2 N 0.46242(13) 0.54429(15) 0.42944(13) 0.0224(3) Uani 1 1 d . . . . .
H2 H 0.520(2) 0.599(2) 0.456(2) 0.025(5) Uiso 1 1 d . . . . .
C1 C 0.24543(15) 0.59092(18) 0.42893(14) 0.0217(3) Uani 1 1 d . . . . .
C2 C 0.21748(18) 0.72064(19) 0.39631(16) 0.0276(4) Uani 1 1 d . . . . .
H2A H 0.279285 0.783584 0.406160 0.033 Uiso 1 1 calc R U . . .
C3 C 0.09389(19) 0.7557(2) 0.34796(17) 0.0340(4) Uani 1 1 d . . . . .
H3 H 0.073067 0.842463 0.324272 0.041 Uiso 1 1 calc R U . . .
C4 C 0.00284(18) 0.6613(2) 0.33545(17) 0.0349(4) Uani 1 1 d . . . . .
H4 H -0.079127 0.685135 0.304152 0.042 Uiso 1 1 calc R U . . .
C5 C 0.03296(16) 0.5320(2) 0.36917(16) 0.0296(4) Uani 1 1 d . . . . .
C6 C 0.15450(16) 0.49439(18) 0.41447(15) 0.0230(3) Uani 1 1 d . . . . .
C7 C 0.33158(15) 0.38053(17) 0.49026(14) 0.0204(3) Uani 1 1 d . . . . .
C8 C 0.36721(15) 0.52765(17) 0.49055(14) 0.0194(3) Uani 1 1 d . . . . .
C9 C 0.41492(15) 0.58236(17) 0.62270(14) 0.0200(3) Uani 1 1 d . . . . .
H9 H 0.428313 0.677395 0.615936 0.024 Uiso 1 1 calc R U . . .
C10 C 0.31757(15) 0.56686(17) 0.69168(14) 0.0208(3) Uani 1 1 d . . . . .
C11 C 0.29929(16) 0.44628(19) 0.74323(15) 0.0251(3) Uani 1 1 d . . . . .
H11 H 0.346624 0.373415 0.735559 0.030 Uiso 1 1 calc R U . . .
C12 C 0.21083(17) 0.4343(2) 0.80598(16) 0.0300(4) Uani 1 1 d . . . . .
H12 H 0.199618 0.353632 0.840218 0.036 Uiso 1 1 calc R U . . .
C13 C 0.13954(17) 0.5415(2) 0.81777(16) 0.0317(4) Uani 1 1 d . . . . .
H13 H 0.079775 0.532883 0.858938 0.038 Uiso 1 1 calc R U . . .
C14 C 0.15757(17) 0.6615(2) 0.76806(16) 0.0320(4) Uani 1 1 d . . . . .
H14 H 0.110321 0.734116 0.776676 0.038 Uiso 1 1 calc R U . . .
C15 C 0.24588(16) 0.67473(19) 0.70517(15) 0.0258(4) Uani 1 1 d . . . . .
H15 H 0.257153 0.756002 0.671926 0.031 Uiso 1 1 calc R U . . .
C16 C 0.53535(15) 0.52422(18) 0.69529(14) 0.0204(3) Uani 1 1 d . . . . .
H16 H 0.543309 0.432853 0.701765 0.024 Uiso 1 1 calc R U . . .
C17 C 0.63089(15) 0.59996(17) 0.75052(14) 0.0217(3) Uani 1 1 d . . . . .
H17 H 0.627010 0.688738 0.728826 0.026 Uiso 1 1 calc R U . . .
C18 C 0.74172(15) 0.55557(18) 0.84262(14) 0.0228(4) Uani 1 1 d . . . . .
C19 C 0.76662(17) 0.4228(2) 0.87242(16) 0.0282(4) Uani 1 1 d . . . . .
H19 H 0.717528 0.357899 0.825564 0.034 Uiso 1 1 calc R U . . .
C20 C 0.86292(18) 0.3859(2) 0.97032(17) 0.0359(5) Uani 1 1 d . . . . .
H20 H 0.877171 0.296971 0.989455 0.043 Uiso 1 1 calc R U . . .
C21 C 0.93849(17) 0.4818(3) 1.04018(17) 0.0392(5) Uani 1 1 d . . . . .
H21 H 1.003262 0.457281 1.106057 0.047 Uiso 1 1 calc R U . . .
C22 C 0.91643(17) 0.6139(3) 1.01082(17) 0.0364(5) Uani 1 1 d . . . . .
H22 H 0.966525 0.678345 1.057319 0.044 Uiso 1 1 calc R U . . .
C23 C 0.81982(16) 0.6508(2) 0.91221(16) 0.0290(4) Uani 1 1 d . . . . .
H23 H 0.806965 0.739693 0.892274 0.035 Uiso 1 1 calc R U . . .
C24 C 0.44039(16) 0.49910(17) 0.31407(15) 0.0215(3) Uani 1 1 d . . . . .
C25 C 0.51641(16) 0.52400(18) 0.13572(14) 0.0238(3) Uani 1 1 d . . . . .
C26 C 0.4115(2) 0.6143(2) 0.07301(18) 0.0336(4) Uani 1 1 d . . . . .
H26A H 0.336407 0.581936 0.085794 0.050 Uiso 1 1 calc R U . . .
H26B H 0.404293 0.616478 -0.012347 0.050 Uiso 1 1 calc R U . . .
H26C H 0.427401 0.701886 0.105839 0.050 Uiso 1 1 calc R U . . .
C27 C 0.49547(19) 0.3829(2) 0.09005(16) 0.0306(4) Uani 1 1 d . . . . .
H27A H 0.557965 0.326849 0.139310 0.046 Uiso 1 1 calc R U . . .
H27B H 0.498942 0.379145 0.007430 0.046 Uiso 1 1 calc R U . . .
H27C H 0.416250 0.353458 0.094499 0.046 Uiso 1 1 calc R U . . .
C28 C 0.6383(2) 0.5754(2) 0.12400(19) 0.0388(5) Uani 1 1 d . . . . .
H28A H 0.652161 0.662839 0.157456 0.058 Uiso 1 1 calc R U . . .
H28B H 0.636767 0.577871 0.039922 0.058 Uiso 1 1 calc R U . . .
H28C H 0.703211 0.518063 0.167180 0.058 Uiso 1 1 calc R U . . .
C29 C 0.14487(19) 0.2437(2) 0.43262(19) 0.0335(4) Uani 1 1 d . . . . .
H29A H 0.124057 0.222437 0.347824 0.050 Uiso 1 1 calc R U . . .
H29B H 0.071358 0.247729 0.458702 0.050 Uiso 1 1 calc R U . . .
H29C H 0.198439 0.176949 0.478005 0.050 Uiso 1 1 calc R U . . .


_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 C5 1.361(2) . ?
O1 C24 1.217(2) . ?
O2 C24 1.343(2) . ?
O2 C25 1.4794(19) . ?
O3 C7 1.222(2) . ?
N1 C6 1.399(2) . ?
N1 C7 1.364(2) . ?
N1 C29 1.454(2) . ?
N2 H2 0.85(2) . ?
N2 C8 1.449(2) . ?
N2 C24 1.357(2) . ?
C1 C2 1.378(3) . ?
C1 C6 1.396(2) . ?
C1 C8 1.508(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.402(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(3) . ?
C5 C6 1.384(2) . ?
C7 C8 1.542(2) . ?
C8 C9 1.563(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.532(2) . ?
C9 C16 1.508(2) . ?
C10 C11 1.396(3) . ?
C10 C15 1.394(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.391(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.335(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.470(2) . ?
C18 C19 1.396(3) . ?
C18 C23 1.399(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.392(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.390(3) . ?
C23 H23 0.9300 . ?
C25 C26 1.514(3) . ?
C25 C27 1.517(3) . ?
C25 C28 1.516(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
C24 O2 C25 119.71(13) . . ?
C6 N1 C29 126.73(14) . . ?
C7 N1 C6 110.34(14) . . ?
C7 N1 C29 121.60(15) . . ?
C8 N2 H2 120.4(15) . . ?
C24 N2 H2 119.2(15) . . ?
C24 N2 C8 118.13(14) . . ?
C2 C1 C6 121.86(16) . . ?
C2 C1 C8 130.07(16) . . ?
C6 C1 C8 107.94(15) . . ?
C1 C2 H2A 120.7 . . ?
C1 C2 C3 118.58(19) . . ?
C3 C2 H2A 120.7 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.04(19) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.39(17) . . ?
C5 C4 H4 119.8 . . ?
F1 C5 C4 119.10(16) . . ?
F1 C5 C6 120.30(18) . . ?
C4 C5 C6 120.60(18) . . ?
C1 C6 N1 110.71(14) . . ?
C5 C6 N1 130.77(17) . . ?
C5 C6 C1 118.51(17) . . ?
O3 C7 N1 125.80(16) . . ?
O3 C7 C8 125.72(15) . . ?
N1 C7 C8 108.45(14) . . ?
N2 C8 C1 115.49(13) . . ?
N2 C8 C7 109.89(14) . . ?
N2 C8 C9 108.88(13) . . ?
C1 C8 C7 101.76(13) . . ?
C1 C8 C9 109.33(13) . . ?
C7 C8 C9 111.36(13) . . ?
C8 C9 H9 106.9 . . ?
C10 C9 C8 111.03(13) . . ?
C10 C9 H9 106.9 . . ?
C16 C9 C8 114.55(13) . . ?
C16 C9 H9 106.9 . . ?
C16 C9 C10 110.18(13) . . ?
C11 C10 C9 121.34(15) . . ?
C15 C10 C9 120.07(16) . . ?
C15 C10 C11 118.59(16) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.49(18) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.44(19) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.57(17) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.52(18) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.40(18) . . ?
C14 C15 H15 119.8 . . ?
C9 C16 H16 119.0 . . ?
C17 C16 C9 121.97(16) . . ?
C17 C16 H16 119.0 . . ?
C16 C17 H17 117.1 . . ?
C16 C17 C18 125.82(16) . . ?
C18 C17 H17 117.1 . . ?
C19 C18 C17 123.02(16) . . ?
C19 C18 C23 118.01(17) . . ?
C23 C18 C17 118.66(17) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.29(19) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.1(2) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.46(18) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.38(19) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 H23 119.6 . . ?
C22 C23 C18 120.7(2) . . ?
C22 C23 H23 119.6 . . ?
O1 C24 O2 126.14(15) . . ?
O1 C24 N2 123.46(16) . . ?
O2 C24 N2 110.37(14) . . ?
O2 C25 C26 108.84(14) . . ?
O2 C25 C27 111.33(14) . . ?
O2 C25 C28 102.08(14) . . ?
C26 C25 C27 112.13(15) . . ?
C26 C25 C28 111.41(17) . . ?
C28 C25 C27 110.60(16) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N1 C29 H29A 109.5 . . ?
N1 C29 H29B 109.5 . . ?
N1 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

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
F1 C5 C6 N1 0.4(3) . . . . ?
F1 C5 C6 C1 -178.26(15) . . . . ?
O3 C7 C8 N2 50.2(2) . . . . ?
O3 C7 C8 C1 173.03(15) . . . . ?
O3 C7 C8 C9 -70.6(2) . . . . ?
N1 C7 C8 N2 -131.74(13) . . . . ?
N1 C7 C8 C1 -8.86(16) . . . . ?
N1 C7 C8 C9 107.53(15) . . . . ?
N2 C8 C9 C10 -179.88(14) . . . . ?
N2 C8 C9 C16 -54.29(19) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C1 C8 C9 C10 53.11(18) . . . . ?
C1 C8 C9 C16 178.70(14) . . . . ?
C2 C1 C6 N1 179.25(15) . . . . ?
C2 C1 C6 C5 -1.8(2) . . . . ?
C2 C1 C8 N2 -57.3(2) . . . . ?
C2 C1 C8 C7 -176.26(17) . . . . ?
C2 C1 C8 C9 65.9(2) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 F1 179.49(17) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 N1 -179.29(17) . . . . ?
C4 C5 C6 C1 2.1(3) . . . . ?
C6 N1 C7 O3 -175.10(16) . . . . ?
C6 N1 C7 C8 6.79(17) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C6 C1 C8 N2 126.80(15) . . . . ?
C6 C1 C8 C7 7.82(16) . . . . ?
C6 C1 C8 C9 -110.04(15) . . . . ?
C7 N1 C6 C1 -1.59(19) . . . . ?
C7 N1 C6 C5 179.68(17) . . . . ?
C7 C8 C9 C10 -58.55(17) . . . . ?
C7 C8 C9 C16 67.04(17) . . . . ?
C8 N2 C24 O1 -6.3(3) . . . . ?
C8 N2 C24 O2 175.43(14) . . . . ?
C8 C1 C2 C3 -175.06(17) . . . . ?
C8 C1 C6 N1 -4.43(18) . . . . ?
C8 C1 C6 C5 174.48(14) . . . . ?
C8 C9 C10 C11 80.07(18) . . . . ?
C8 C9 C10 C15 -100.62(18) . . . . ?
C8 C9 C16 C17 126.77(17) . . . . ?
C9 C10 C11 C12 179.71(15) . . . . ?
C9 C10 C15 C14 -179.78(15) . . . . ?
C9 C16 C17 C18 166.58(15) . . . . ?
C10 C9 C16 C17 -107.20(18) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C10 C15 C14 -0.4(2) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C10 -0.1(3) . . . . ?
C15 C10 C11 C12 0.4(2) . . . . ?
C16 C9 C10 C11 -47.9(2) . . . . ?
C16 C9 C10 C15 131.39(16) . . . . ?
C16 C17 C18 C19 8.3(3) . . . . ?
C16 C17 C18 C23 -165.10(17) . . . . ?
C17 C18 C19 C20 -171.25(16) . . . . ?
C17 C18 C23 C22 171.38(16) . . . . ?
C18 C19 C20 C21 -1.0(3) . . . . ?
C19 C18 C23 C22 -2.4(2) . . . . ?
C19 C20 C21 C22 0.0(3) . . . . ?
C20 C21 C22 C23 -0.2(3) . . . . ?
C21 C22 C23 C18 1.4(3) . . . . ?
C23 C18 C19 C20 2.2(3) . . . . ?
C24 O2 C25 C26 58.7(2) . . . . ?
C24 O2 C25 C27 -65.4(2) . . . . ?
C24 O2 C25 C28 176.54(16) . . . . ?
C24 N2 C8 C1 -58.5(2) . . . . ?
C24 N2 C8 C7 55.84(19) . . . . ?
C24 N2 C8 C9 178.05(15) . . . . ?
C25 O2 C24 O1 17.8(3) . . . . ?
C25 O2 C24 N2 -163.90(15) . . . . ?
C29 N1 C6 C1 -168.44(16) . . . . ?
C29 N1 C6 C5 12.8(3) . . . . ?
C29 N1 C7 O3 -7.5(2) . . . . ?
C29 N1 C7 C8 174.44(15) . . . . ?

_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 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.669
####################################################################### 
# 
# 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_zc-2-2
_database_code_depnum_ccdc_archive 'CCDC 2038580'
_audit_update_record             
;
2020-10-15 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2020-03-06
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H29 F N2 O3'
_chemical_formula_sum            'C29 H29 F N2 O3'
_chemical_formula_weight         472.54
_chemical_absolute_configuration ad
_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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   25.4371(5)
_cell_length_b                   6.95612(16)
_cell_length_c                   15.3764(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.6850(16)
_cell_angle_gamma                90
_cell_volume                     2681.98(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6502
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.5800
_cell_measurement_theta_min      2.9060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79080
_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    1.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.13
_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  0.0168
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10381
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.708
_diffrn_reflns_theta_min         2.915
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -35.00   1.00    1.00    --  -40.98 -57.00   0.00   27
  2  ω     23.00  71.00   1.00    1.00    --   40.98  57.00   0.00   48
  3  ω      9.00 117.00   1.00    1.00    --   40.98  77.00 -90.00  108
  4  ω     50.00  77.00   1.00    1.00    --   40.98  37.00   0.00   27
  5  ω    -35.00  37.00   1.00    1.00    --   40.98 -77.00  60.00   72
  6  ω     81.00 114.00   1.00    1.00    --   40.98  37.00   0.00   33
  7  ω     40.00  67.00   1.00    1.00    --   40.98  77.00-150.00   27
  8  ω     30.00  87.00   1.00    1.00    --   40.98  37.00-120.00   57
  9  ω      1.00  79.00   1.00    1.00    --   40.98 -99.00 150.00   78
 10  ω     75.00 100.00   1.00    2.00    --  106.95  77.00 -30.00   25
 11  ω    109.00 178.00   1.00    2.00    --  106.95  77.00-120.00   69
 12  ω     75.00 100.00   1.00    1.50    --  106.95  77.00-120.00   25
 13  ω     74.00 101.00   1.00    1.50    --  106.95  77.00   0.00   27
 14  ω     74.00 100.00   1.00    1.50    --  106.95  77.00 -60.00   26
 15  ω     34.00  87.00   1.00    1.50    --  106.95-124.00-180.00   53
 16  ω     74.00 101.00   1.00    1.50    --  106.95  77.00-150.00   27
 17  ω     24.00 106.00   1.00    1.50    --  106.95 -94.00-180.00   82
 18  ω     78.00 104.00   1.00    1.50    --  106.95  61.00 -90.00   26
 19  ω     78.00 104.00   1.00    1.50    --  106.95  61.00   0.00   26
 20  ω     79.00 140.00   1.00    1.50    --  106.95  61.00 -60.00   61
 21  ω     79.00 104.00   1.00    1.50    --  106.95  61.00 -30.00   25
 22  ω     82.00 109.00   1.00    1.50    --  106.95  61.00-150.00   27
 23  ω     82.00 145.00   1.00    1.50    --  106.95  45.00 -30.00   63
 24  ω     79.00 104.00   1.00    1.50    --  106.95  61.00-120.00   25
 25  ω     82.00 149.00   1.00    1.50    --  106.95  45.00-120.00   67
 26  ω     81.00 108.00   1.00    1.50    --  106.95  45.00 -60.00   27
 27  ω     81.00 178.00   1.00    1.50    --  106.95  45.00   0.00   97
 28  ω     24.00  69.00   1.00    1.50    --  106.95 -94.00 -90.00   45
;
_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      0.0078301000
_diffrn_orient_matrix_UB_12      0.0120649000
_diffrn_orient_matrix_UB_13      -0.0970437000
_diffrn_orient_matrix_UB_21      -0.0605189000
_diffrn_orient_matrix_UB_22      -0.0245871000
_diffrn_orient_matrix_UB_23      -0.0301519000
_diffrn_orient_matrix_UB_31      -0.0072132000
_diffrn_orient_matrix_UB_32      0.2197350000
_diffrn_orient_matrix_UB_33      0.0019726000
_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         0.675
_reflns_Friedel_fraction_full    0.821
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                4489
_reflns_number_total             4740
_reflns_odcompleteness_completeness 98.13
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details 
;
 Flack x determined using 1690 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_coef       0.00110(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.033
_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)+(0.0499P)²+0.3009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0907
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C)
;
_atom_sites_solution_hydrogens   mixed
_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
F1 F 0.66568(6) 0.4129(3) 1.07656(8) 0.0817(5) Uani 1 1 d . . . . .
O1 O 0.59884(8) 0.0505(2) 0.77954(11) 0.0768(5) Uani 1 1 d . . . . .
O2 O 0.72450(7) 0.1617(3) 0.79533(10) 0.0747(5) Uani 1 1 d . . . . .
O3 O 0.73351(6) 0.2139(3) 0.65237(10) 0.0720(5) Uani 1 1 d . . . . .
N1 N 0.62562(7) 0.2348(3) 0.90312(10) 0.0559(4) Uani 1 1 d . . . . .
N2 N 0.66480(7) 0.3365(3) 0.70241(11) 0.0568(4) Uani 1 1 d . . . . .
H2 H 0.6579(10) 0.392(4) 0.6490(17) 0.070(7) Uiso 1 1 d . . . . .
C1 C 0.65643(7) 0.5053(3) 0.84227(12) 0.0477(4) Uani 1 1 d . . . . .
C2 C 0.68257(8) 0.6774(3) 0.84290(14) 0.0587(5) Uani 1 1 d . . . . .
H2A H 0.686533 0.737202 0.790298 0.070 Uiso 1 1 calc R U . . .
C3 C 0.70311(9) 0.7611(4) 0.92353(16) 0.0733(7) Uani 1 1 d . . . . .
H3 H 0.720939 0.878076 0.924914 0.088 Uiso 1 1 calc R U . . .
C4 C 0.69726(9) 0.6723(4) 1.00147(16) 0.0719(7) Uani 1 1 d . . . . .
H4 H 0.711152 0.728938 1.055223 0.086 Uiso 1 1 calc R U . . .
C5 C 0.67095(8) 0.5005(4) 0.99941(13) 0.0597(6) Uani 1 1 d . . . . .
C6 C 0.65044(7) 0.4137(3) 0.92058(12) 0.0488(4) Uani 1 1 d . . . . .
C7 C 0.61738(9) 0.1970(3) 0.81488(13) 0.0551(5) Uani 1 1 d . . . . .
C8 C 0.63128(7) 0.3794(3) 0.76674(11) 0.0470(4) Uani 1 1 d . . . . .
C9 C 0.57686(7) 0.4568(3) 0.71487(12) 0.0491(4) Uani 1 1 d . . . . .
H9 H 0.562350 0.355069 0.673621 0.059 Uiso 1 1 calc R U . . .
C10 C 0.58488(7) 0.6289(3) 0.66000(12) 0.0498(4) Uani 1 1 d . . . . .
H10 H 0.597665 0.741259 0.688872 0.060 Uiso 1 1 calc R U . . .
C11 C 0.57476(7) 0.6299(3) 0.57262(12) 0.0533(5) Uani 1 1 d . . . . .
H11 H 0.562602 0.515210 0.545300 0.064 Uiso 1 1 calc R U . . .
C12 C 0.58070(8) 0.7930(4) 0.51426(12) 0.0549(5) Uani 1 1 d . . . . .
C13 C 0.55904(9) 0.7796(5) 0.42513(14) 0.0705(7) Uani 1 1 d . . . . .
H13 H 0.541334 0.668022 0.403531 0.085 Uiso 1 1 calc R U . . .
C14 C 0.56358(11) 0.9304(6) 0.36846(16) 0.0870(9) Uani 1 1 d . . . . .
H14 H 0.548127 0.920701 0.309352 0.104 Uiso 1 1 calc R U . . .
C15 C 0.59059(13) 1.0937(5) 0.39842(18) 0.0905(9) Uani 1 1 d . . . . .
H15 H 0.593772 1.194586 0.359938 0.109 Uiso 1 1 calc R U . . .
C16 C 0.61305(15) 1.1074(5) 0.48619(18) 0.0929(9) Uani 1 1 d . . . . .
H16 H 0.631900 1.217263 0.506973 0.112 Uiso 1 1 calc R U . . .
C17 C 0.60770(12) 0.9593(4) 0.54310(14) 0.0753(7) Uani 1 1 d . . . . .
H17 H 0.622603 0.971405 0.602369 0.090 Uiso 1 1 calc R U . . .
C18 C 0.53594(7) 0.4912(3) 0.77491(12) 0.0533(5) Uani 1 1 d . . . . .
C19 C 0.53415(9) 0.6599(4) 0.82098(15) 0.0633(5) Uani 1 1 d . . . . .
H19 H 0.558711 0.756554 0.815931 0.076 Uiso 1 1 calc R U . . .
C20 C 0.49618(11) 0.6878(5) 0.87493(18) 0.0841(8) Uani 1 1 d . . . . .
H20 H 0.495671 0.802228 0.906080 0.101 Uiso 1 1 calc R U . . .
C21 C 0.45936(12) 0.5468(7) 0.8824(2) 0.0988(11) Uani 1 1 d . . . . .
H21 H 0.433806 0.565419 0.918281 0.119 Uiso 1 1 calc R U . . .
C22 C 0.46062(12) 0.3799(7) 0.8369(2) 0.1044(12) Uani 1 1 d . . . . .
H22 H 0.435766 0.284171 0.841794 0.125 Uiso 1 1 calc R U . . .
C23 C 0.49839(10) 0.3508(5) 0.78331(18) 0.0808(8) Uani 1 1 d . . . . .
H23 H 0.498645 0.235809 0.752548 0.097 Uiso 1 1 calc R U . . .
C24 C 0.60841(14) 0.1062(4) 0.96705(17) 0.0872(9) Uani 1 1 d . . . . .
H24A H 0.637627 0.082272 1.014045 0.131 Uiso 1 1 calc R U . . .
H24B H 0.596640 -0.013026 0.938853 0.131 Uiso 1 1 calc R U . . .
H24C H 0.579557 0.164205 0.990578 0.131 Uiso 1 1 calc R U . . .
C25 C 0.70980(9) 0.2302(4) 0.72334(13) 0.0574(5) Uani 1 1 d . . . . .
C26 C 0.78321(10) 0.1029(5) 0.65622(18) 0.0848(9) Uani 1 1 d . . . . .
C27 C 0.79370(14) 0.1221(7) 0.5624(2) 0.1138(13) Uani 1 1 d . . . . .
H27A H 0.763138 0.077827 0.522033 0.171 Uiso 1 1 calc R U . . .
H27B H 0.824224 0.046186 0.555362 0.171 Uiso 1 1 calc R U . . .
H27C H 0.800375 0.254482 0.550296 0.171 Uiso 1 1 calc R U . . .
C28 C 0.77357(18) -0.1045(6) 0.6786(3) 0.1268(15) Uani 1 1 d . . . . .
H28B H 0.803569 -0.181068 0.669486 0.190 Uiso 1 1 calc R U . . .
H28A H 0.742007 -0.150461 0.641204 0.190 Uiso 1 1 calc R U . . .
H28C H 0.769011 -0.113487 0.739138 0.190 Uiso 1 1 calc R U . . .
C29 C 0.82699(13) 0.1975(8) 0.7211(2) 0.1267(16) Uani 1 1 d . . . . .
H29A H 0.828697 0.331732 0.707383 0.190 Uiso 1 1 calc R U . . .
H29B H 0.860530 0.137776 0.717116 0.190 Uiso 1 1 calc R U . . .
H29C H 0.819491 0.182818 0.779860 0.190 Uiso 1 1 calc R U . . .


_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 C5 1.360(3) . ?
O1 C7 1.212(3) . ?
O2 C25 1.206(2) . ?
O3 C25 1.337(2) . ?
O3 C26 1.474(3) . ?
N1 C6 1.401(3) . ?
N1 C7 1.363(3) . ?
N1 C24 1.450(3) . ?
N2 H2 0.90(3) . ?
N2 C8 1.442(2) . ?
N2 C25 1.355(3) . ?
C1 C2 1.368(3) . ?
C1 C6 1.393(3) . ?
C1 C8 1.509(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.390(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(4) . ?
C5 C6 1.376(3) . ?
C7 C8 1.540(3) . ?
C8 C9 1.572(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.498(3) . ?
C9 C18 1.522(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.325(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.470(3) . ?
C12 C13 1.392(3) . ?
C12 C17 1.380(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.367(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(3) . ?
C18 C23 1.387(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.359(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.381(4) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C26 C27 1.517(4) . ?
C26 C28 1.513(6) . ?
C26 C29 1.514(5) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
C25 O3 C26 120.87(17) . . ?
C6 N1 C24 126.57(19) . . ?
C7 N1 C6 110.53(16) . . ?
C7 N1 C24 122.9(2) . . ?
C8 N2 H2 119.4(17) . . ?
C25 N2 H2 118.7(16) . . ?
C25 N2 C8 121.57(17) . . ?
C2 C1 C6 121.19(18) . . ?
C2 C1 C8 131.00(18) . . ?
C6 C1 C8 107.80(17) . . ?
C1 C2 H2A 120.6 . . ?
C1 C2 C3 118.8(2) . . ?
C3 C2 H2A 120.6 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
F1 C5 C4 119.4(2) . . ?
F1 C5 C6 119.6(2) . . ?
C4 C5 C6 121.0(2) . . ?
C1 C6 N1 110.63(16) . . ?
C5 C6 N1 130.58(19) . . ?
C5 C6 C1 118.7(2) . . ?
O1 C7 N1 126.2(2) . . ?
O1 C7 C8 125.49(18) . . ?
N1 C7 C8 108.09(17) . . ?
N2 C8 C1 115.17(16) . . ?
N2 C8 C7 111.68(17) . . ?
N2 C8 C9 107.14(15) . . ?
C1 C8 C7 102.15(15) . . ?
C1 C8 C9 114.51(16) . . ?
C7 C8 C9 105.80(15) . . ?
C8 C9 H9 106.5 . . ?
C10 C9 C8 111.58(15) . . ?
C10 C9 H9 106.5 . . ?
C10 C9 C18 112.80(17) . . ?
C18 C9 C8 112.32(15) . . ?
C18 C9 H9 106.5 . . ?
C9 C10 H10 118.2 . . ?
C11 C10 C9 123.6(2) . . ?
C11 C10 H10 118.2 . . ?
C10 C11 H11 116.5 . . ?
C10 C11 C12 126.9(2) . . ?
C12 C11 H11 116.5 . . ?
C13 C12 C11 119.0(2) . . ?
C17 C12 C11 123.20(18) . . ?
C17 C12 C13 117.8(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.3(3) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.3 . . ?
C16 C17 C12 121.4(2) . . ?
C16 C17 H17 119.3 . . ?
C19 C18 C9 122.14(19) . . ?
C19 C18 C23 118.0(2) . . ?
C23 C18 C9 119.8(2) . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 120.9(2) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.7(3) . . ?
C23 C22 H22 119.6 . . ?
C18 C23 H23 119.6 . . ?
C22 C23 C18 120.8(3) . . ?
C22 C23 H23 119.6 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O2 C25 O3 127.1(2) . . ?
O2 C25 N2 123.58(19) . . ?
O3 C25 N2 109.35(17) . . ?
O3 C26 C27 101.7(2) . . ?
O3 C26 C28 109.8(3) . . ?
O3 C26 C29 109.3(3) . . ?
C28 C26 C27 111.2(3) . . ?
C28 C26 C29 113.2(3) . . ?
C29 C26 C27 111.1(3) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28B C28 H28A 109.5 . . ?
H28B C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

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
F1 C5 C6 N1 -3.8(3) . . . . ?
F1 C5 C6 C1 -179.77(17) . . . . ?
O1 C7 C8 N2 -52.0(3) . . . . ?
O1 C7 C8 C1 -175.6(2) . . . . ?
O1 C7 C8 C9 64.2(3) . . . . ?
N1 C7 C8 N2 132.65(18) . . . . ?
N1 C7 C8 C1 9.0(2) . . . . ?
N1 C7 C8 C9 -111.10(18) . . . . ?
N2 C8 C9 C10 -57.2(2) . . . . ?
N2 C8 C9 C18 175.01(17) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C1 C8 C9 C10 71.9(2) . . . . ?
C1 C8 C9 C18 -55.9(2) . . . . ?
C2 C1 C6 N1 -176.05(18) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C8 N2 50.3(3) . . . . ?
C2 C1 C8 C7 171.6(2) . . . . ?
C2 C1 C8 C9 -74.6(3) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 F1 179.5(2) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 N1 175.2(2) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C6 N1 C7 O1 176.6(2) . . . . ?
C6 N1 C7 C8 -8.1(2) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C6 C1 C8 N2 -128.07(18) . . . . ?
C6 C1 C8 C7 -6.8(2) . . . . ?
C6 C1 C8 C9 107.02(18) . . . . ?
C7 N1 C6 C1 3.6(2) . . . . ?
C7 N1 C6 C5 -172.6(2) . . . . ?
C7 C8 C9 C10 -176.47(15) . . . . ?
C7 C8 C9 C18 55.7(2) . . . . ?
C8 N2 C25 O2 1.4(4) . . . . ?
C8 N2 C25 O3 -179.3(2) . . . . ?
C8 C1 C2 C3 -178.6(2) . . . . ?
C8 C1 C6 N1 2.5(2) . . . . ?
C8 C1 C6 C5 179.26(17) . . . . ?
C8 C9 C10 C11 114.2(2) . . . . ?
C8 C9 C18 C19 85.0(2) . . . . ?
C8 C9 C18 C23 -96.0(2) . . . . ?
C9 C10 C11 C12 178.91(18) . . . . ?
C9 C18 C19 C20 179.6(2) . . . . ?
C9 C18 C23 C22 -179.4(3) . . . . ?
C10 C9 C18 C19 -42.2(3) . . . . ?
C10 C9 C18 C23 136.8(2) . . . . ?
C10 C11 C12 C13 -168.2(2) . . . . ?
C10 C11 C12 C17 13.0(3) . . . . ?
C11 C12 C13 C14 179.6(2) . . . . ?
C11 C12 C17 C16 179.0(3) . . . . ?
C12 C13 C14 C15 1.6(4) . . . . ?
C13 C12 C17 C16 0.2(4) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C14 C15 C16 C17 -0.9(5) . . . . ?
C15 C16 C17 C12 1.0(5) . . . . ?
C17 C12 C13 C14 -1.5(4) . . . . ?
C18 C9 C10 C11 -118.3(2) . . . . ?
C18 C19 C20 C21 -0.6(4) . . . . ?
C19 C18 C23 C22 -0.4(4) . . . . ?
C19 C20 C21 C22 0.3(5) . . . . ?
C20 C21 C22 C23 0.0(6) . . . . ?
C21 C22 C23 C18 0.1(5) . . . . ?
C23 C18 C19 C20 0.6(4) . . . . ?
C24 N1 C6 C1 -174.0(2) . . . . ?
C24 N1 C6 C5 9.8(4) . . . . ?
C24 N1 C7 O1 -5.6(4) . . . . ?
C24 N1 C7 C8 169.7(2) . . . . ?
C25 O3 C26 C27 178.9(3) . . . . ?
C25 O3 C26 C28 61.1(4) . . . . ?
C25 O3 C26 C29 -63.6(3) . . . . ?
C25 N2 C8 C1 65.4(3) . . . . ?
C25 N2 C8 C7 -50.5(3) . . . . ?
C25 N2 C8 C9 -165.91(19) . . . . ?
C26 O3 C25 O2 0.0(4) . . . . ?
C26 O3 C25 N2 -179.2(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.347
_oxdiff_exptl_absorpt_empirical_full_min 0.656
