# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_chem_veerendrak_i2_48_17_07_0m
_database_code_depnum_ccdc_archive 'CCDC 1048304'

_audit_update_record             
;
2015-02-07 deposited with the CCDC.
2015-04-23 downloaded from the CCDC.
;
_publcif_datablock.id            {d9b07c30-3a98-4eff-bcb3-cd4b27cf2817}

# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H23 F N2 O3'
_chemical_formula_weight         454.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P121/c1

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

_cell_length_a                   9.0223(2)
_cell_length_b                   9.0135(2)
_cell_length_c                   28.2468(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.2010(10)
_cell_angle_gamma                90.00
_cell_volume                     2295.41(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13460
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         24.11
_reflns_number_total             3654
_reflns_number_gt                2863
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0496P)²+0.8138P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3654
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1134
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.264
_refine_ls_shift/su_mean         0.022

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.0645(2) 0.9275(2) 0.55489(5) 0.1093(6) Uani 1 1 d . . .
O1 O -0.3287(3) 1.8793(2) 0.38736(8) 0.1162(8) Uani 1 1 d . . .
O2 O -0.0140(2) 1.30077(18) 0.27083(5) 0.0727(5) Uani 1 1 d . . .
O3 O -0.3439(2) 1.7454(2) 0.44906(7) 0.0937(6) Uani 1 1 d . . .
N1 N -0.3056(2) 1.7661(3) 0.40878(8) 0.0730(6) Uani 1 1 d . . .
N2 N 0.35324(19) 0.57068(18) 0.32418(5) 0.0495(4) Uani 1 1 d . . .
C1 C -0.2278(2) 1.6452(3) 0.38495(7) 0.0522(5) Uani 1 1 d . . .
C2 C -0.2428(2) 1.5041(3) 0.40185(8) 0.0570(6) Uani 1 1 d . . .
H2 H -0.3000 1.4848 0.4278 0.068 Uiso 1 1 calc R . .
C3 C -0.1703(2) 1.3912(2) 0.37915(7) 0.0529(5) Uani 1 1 d . . .
H3 H -0.1780 1.2943 0.3902 0.064 Uiso 1 1 calc R . .
C4 C -0.0861(2) 1.4202(2) 0.34010(6) 0.0441(5) Uani 1 1 d . . .
C5 C -0.0142(2) 1.2970(2) 0.31402(7) 0.0473(5) Uani 1 1 d . . .
C6 C 0.0535(2) 1.1768(2) 0.34143(7) 0.0551(6) Uani 1 1 d . . .
H6 H 0.0561 1.1846 0.3743 0.066 Uiso 1 1 calc R . .
C7 C 0.1117(2) 1.0568(2) 0.32257(7) 0.0446(5) Uani 1 1 d . . .
H7 H 0.1084 1.0500 0.2897 0.054 Uiso 1 1 calc R . .
C8 C 0.1789(2) 0.9373(2) 0.34842(7) 0.0515(5) Uani 1 1 d . . .
H8 H 0.1852 0.9443 0.3813 0.062 Uiso 1 1 calc R . .
C9 C 0.2330(2) 0.8168(2) 0.32862(7) 0.0469(5) Uani 1 1 d . . .
H9 H 0.2321 0.8173 0.2957 0.056 Uiso 1 1 calc R . .
C10 C 0.2931(2) 0.6848(2) 0.35104(6) 0.0449(5) Uani 1 1 d . . .
C11 C 0.2879(2) 0.6392(2) 0.39764(6) 0.0458(5) Uani 1 1 d . . .
C12 C 0.2285(2) 0.7181(2) 0.43883(7) 0.0478(5) Uani 1 1 d . . .
C13 C 0.1011(2) 0.6677(3) 0.45935(8) 0.0649(6) Uani 1 1 d . . .
H13 H 0.0522 0.5852 0.4467 0.078 Uiso 1 1 calc R . .
C14 C 0.0452(3) 0.7379(4) 0.49838(9) 0.0786(8) Uani 1 1 d . . .
H14 H -0.0411 0.7042 0.5118 0.094 Uiso 1 1 calc R . .
C15 C 0.1198(3) 0.8575(3) 0.51656(8) 0.0737(8) Uani 1 1 d . . .
C16 C 0.3001(2) 0.8389(3) 0.45932(7) 0.0587(6) Uani 1 1 d . . .
H16 H 0.3869 0.8732 0.4464 0.070 Uiso 1 1 calc R . .
C17 C 0.2462(3) 0.9103(3) 0.49850(8) 0.0689(7) Uani 1 1 d . . .
H17 H 0.2952 0.9917 0.5119 0.083 Uiso 1 1 calc R . .
C18 C 0.3441(2) 0.4919(2) 0.39972(7) 0.0504(5) Uani 1 1 d . . .
C19 C 0.3666(3) 0.3914(3) 0.43719(9) 0.0662(6) Uani 1 1 d . . .
H19 H 0.3419 0.4169 0.4678 0.079 Uiso 1 1 calc R . .
C20 C 0.4252(3) 0.2558(3) 0.42796(10) 0.0773(8) Uani 1 1 d . . .
H20 H 0.4400 0.1882 0.4526 0.093 Uiso 1 1 calc R . .
C21 C 0.4635(3) 0.2164(3) 0.38242(10) 0.0724(7) Uani 1 1 d . . .
H21 H 0.5030 0.1228 0.3772 0.087 Uiso 1 1 calc R . .
C22 C 0.4443(3) 0.3121(2) 0.34516(9) 0.0618(6) Uani 1 1 d . . .
H22 H 0.4702 0.2849 0.3148 0.074 Uiso 1 1 calc R . .
C23 C 0.3844(2) 0.4521(2) 0.35404(7) 0.0508(5) Uani 1 1 d . . .
C24 C -0.1436(2) 1.6792(2) 0.34661(7) 0.0529(5) Uani 1 1 d . . .
H24 H -0.1344 1.7767 0.3363 0.063 Uiso 1 1 calc R . .
C25 C -0.0739(2) 1.5655(2) 0.32408(7) 0.0498(5) Uani 1 1 d . . .
H25 H -0.0179 1.5857 0.2979 0.060 Uiso 1 1 calc R . .
C26 C 0.3917(2) 0.5807(3) 0.27393(7) 0.0532(5) Uani 1 1 d . . .
H26 H 0.3709 0.6831 0.2640 0.064 Uiso 1 1 calc R . .
C27 C 0.2951(3) 0.4831(4) 0.24264(9) 0.0864(9) Uani 1 1 d . . .
H27A H 0.3094 0.3813 0.2517 0.130 Uiso 1 1 calc R . .
H27B H 0.3212 0.4958 0.2103 0.130 Uiso 1 1 calc R . .
H27C H 0.1930 0.5098 0.2459 0.130 Uiso 1 1 calc R . .
C28 C 0.5551(3) 0.5561(3) 0.26780(9) 0.0792(8) Uani 1 1 d . . .
H28A H 0.6108 0.6291 0.2857 0.119 Uiso 1 1 calc R . .
H28B H 0.5765 0.5648 0.2349 0.119 Uiso 1 1 calc R . .
H28C H 0.5820 0.4588 0.2789 0.119 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C15 1.364(3) . ?
O1 N1 1.201(3) . ?
O2 C5 1.220(2) . ?
O3 N1 1.216(3) . ?
N1 C1 1.473(3) . ?
N2 C23 1.384(2) . ?
N2 C10 1.400(2) . ?
N2 C26 1.477(2) . ?
C1 C2 1.367(3) . ?
C1 C24 1.381(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C25 1.391(3) . ?
C4 C5 1.495(3) . ?
C5 C6 1.453(3) . ?
C6 C7 1.322(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.424(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.323(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.444(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(3) . ?
C11 C18 1.422(3) . ?
C11 C12 1.481(3) . ?
C12 C16 1.381(3) . ?
C12 C13 1.384(3) . ?
C13 C14 1.383(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(4) . ?
C14 H14 0.9300 . ?
C15 C17 1.353(4) . ?
C16 C17 1.385(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.401(3) . ?
C18 C19 1.402(3) . ?
C19 C20 1.361(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.391(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.367(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.399(3) . ?
C22 H22 0.9300 . ?
C24 C25 1.372(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.502(3) . ?
C26 C28 1.507(3) . ?
C26 H26 0.9800 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
O1 N1 O3 123.5(2) . . ?
O1 N1 C1 118.4(2) . . ?
O3 N1 C1 118.1(2) . . ?
C23 N2 C10 108.14(15) . . ?
C23 N2 C26 125.69(17) . . ?
C10 N2 C26 125.87(16) . . ?
C2 C1 C24 123.1(2) . . ?
C2 C1 N1 118.2(2) . . ?
C24 C1 N1 118.7(2) . . ?
C1 C2 C3 117.94(19) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C25 119.27(19) . . ?
C3 C4 C5 120.86(18) . . ?
C25 C4 C5 119.82(17) . . ?
O2 C5 C6 122.47(19) . . ?
O2 C5 C4 119.29(18) . . ?
C6 C5 C4 118.24(16) . . ?
C7 C6 C5 124.07(18) . . ?
C7 C6 H6 118.0 . . ?
C5 C6 H6 118.0 . . ?
C6 C7 C8 125.43(18) . . ?
C6 C7 H7 117.3 . . ?
C8 C7 H7 117.3 . . ?
C9 C8 C7 124.11(18) . . ?
C9 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
C8 C9 C10 128.99(18) . . ?
C8 C9 H9 115.5 . . ?
C10 C9 H9 115.5 . . ?
C11 C10 N2 109.00(17) . . ?
C11 C10 C9 129.59(18) . . ?
N2 C10 C9 120.99(16) . . ?
C10 C11 C18 107.00(17) . . ?
C10 C11 C12 129.20(18) . . ?
C18 C11 C12 123.71(17) . . ?
C16 C12 C13 117.7(2) . . ?
C16 C12 C11 122.02(18) . . ?
C13 C12 C11 120.2(2) . . ?
C14 C13 C12 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 118.2(2) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C17 C15 C14 123.2(2) . . ?
C17 C15 F1 118.4(3) . . ?
C14 C15 F1 118.3(3) . . ?
C12 C16 C17 121.9(2) . . ?
C12 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C15 C17 C16 117.7(3) . . ?
C15 C17 H17 121.2 . . ?
C16 C17 H17 121.2 . . ?
C23 C18 C19 119.6(2) . . ?
C23 C18 C11 107.83(17) . . ?
C19 C18 C11 132.5(2) . . ?
C20 C19 C18 118.8(2) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C20 C21 121.3(2) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C22 C21 C20 121.5(2) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 118.0(2) . . ?
C21 C22 H22 121.0 . . ?
C23 C22 H22 121.0 . . ?
N2 C23 C22 131.16(19) . . ?
N2 C23 C18 108.03(17) . . ?
C22 C23 C18 120.8(2) . . ?
C25 C24 C1 118.3(2) . . ?
C25 C24 H24 120.9 . . ?
C1 C24 H24 120.9 . . ?
C24 C25 C4 120.57(19) . . ?
C24 C25 H25 119.7 . . ?
C4 C25 H25 119.7 . . ?
N2 C26 C27 112.16(19) . . ?
N2 C26 C28 111.62(17) . . ?
C27 C26 C28 113.2(2) . . ?
N2 C26 H26 106.4 . . ?
C27 C26 H26 106.4 . . ?
C28 C26 H26 106.4 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.11
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.035
_vrf_THETM01_I                   
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6].
RESPONSE: The crystal was poorly diffracting at higher Bragg angles.
The situation did not improve even after recrystallisation and
fresh data collection.
;

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
####################################################################### 
# 
# 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_chem_veerendra_i2_50_20_07_0m
_database_code_depnum_ccdc_archive 'CCDC 1048305'

_audit_update_record             
;
2015-02-07 deposited with the CCDC.
2015-04-23 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H24 F N O2'
_chemical_formula_sum            'C28 H24 F N O2'
_chemical_formula_weight         425.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P12(1)/n1

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

_cell_length_a                   8.0748(6)
_cell_length_b                   19.8897(15)
_cell_length_c                   14.2381(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.183(5)
_cell_angle_gamma                90.00
_cell_volume                     2285.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10625
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         20.33
_reflns_number_total             2219
_reflns_number_gt                1841
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0790P)²+0.9721P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2219
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1253
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.090
_refine_ls_shift/su_mean         0.017

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.2719(3) 0.02377(12) 0.45835(16) 0.1263(8) Uani 1 1 d . . .
O1 O 1.1131(3) 0.19585(12) 0.67759(16) 0.0969(8) Uani 1 1 d . . .
O2 O 1.2106(3) 0.16801(13) 0.84313(16) 0.0973(8) Uani 1 1 d . . .
H2 H 1.1976 0.1910 0.7956 0.146 Uiso 1 1 calc R . .
N1 N 0.9279(3) 0.20337(12) 0.16450(19) 0.0694(7) Uani 1 1 d . . .
C1 C 0.3774(4) 0.0534(2) 0.3979(2) 0.0845(10) Uani 1 1 d . . .
C2 C 0.3959(4) 0.1205(2) 0.4010(2) 0.0842(10) Uani 1 1 d . . .
H2A H 0.3373 0.1465 0.4427 0.101 Uiso 1 1 calc R . .
C3 C 0.5042(4) 0.14970(16) 0.3408(2) 0.0728(9) Uani 1 1 d . . .
H3 H 0.5187 0.1961 0.3425 0.087 Uiso 1 1 calc R . .
C4 C 0.5920(3) 0.11229(15) 0.27770(19) 0.0590(8) Uani 1 1 d . . .
C5 C 0.7107(3) 0.14420(14) 0.2156(2) 0.0582(8) Uani 1 1 d . . .
C6 C 0.8501(4) 0.17989(13) 0.2432(2) 0.0595(8) Uani 1 1 d . . .
C7 C 0.9178(3) 0.19262(15) 0.3371(2) 0.0648(8) Uani 1 1 d . . .
H7 H 0.9675 0.2342 0.3481 0.078 Uiso 1 1 calc R . .
C8 C 0.9148(3) 0.14973(15) 0.4092(2) 0.0668(8) Uani 1 1 d . . .
H8 H 0.8668 0.1078 0.3986 0.080 Uiso 1 1 calc R . .
C9 C 0.9807(3) 0.16424(15) 0.5014(2) 0.0655(8) Uani 1 1 d . . .
H9 H 1.0240 0.2070 0.5123 0.079 Uiso 1 1 calc R . .
C10 C 0.9847(4) 0.12114(15) 0.5728(2) 0.0675(8) Uani 1 1 d . . .
H10 H 0.9402 0.0784 0.5635 0.081 Uiso 1 1 calc R . .
C11 C 1.0559(4) 0.13833(16) 0.6648(2) 0.0672(8) Uani 1 1 d . . .
C12 C 1.0624(3) 0.09011(14) 0.7420(2) 0.0617(8) Uani 1 1 d . . .
C13 C 0.9904(4) 0.02635(16) 0.7347(2) 0.0778(9) Uani 1 1 d . . .
H13 H 0.9362 0.0139 0.6786 0.093 Uiso 1 1 calc R . .
C14 C 0.9977(5) -0.01802(18) 0.8077(3) 0.0942(11) Uani 1 1 d . . .
H14 H 0.9475 -0.0600 0.8017 0.113 Uiso 1 1 calc R . .
C15 C 1.0806(5) 0.0000(2) 0.8906(3) 0.0951(12) Uani 1 1 d . . .
H15 H 1.0880 -0.0305 0.9401 0.114 Uiso 1 1 calc R . .
C16 C 1.0853(4) 0.24067(17) 0.1644(3) 0.0961(11) Uani 1 1 d . . .
H16 H 1.1126 0.2409 0.2321 0.115 Uiso 1 1 calc R . .
C17 C 1.0626(5) 0.31290(17) 0.1493(3) 0.1035(12) Uani 1 1 d . . .
H17A H 1.1667 0.3355 0.1597 0.155 Uiso 1 1 calc R . .
H17B H 0.9841 0.3299 0.1924 0.155 Uiso 1 1 calc R . .
H17C H 1.0221 0.3207 0.0860 0.155 Uiso 1 1 calc R . .
C18 C 1.2230(4) 0.2040(2) 0.1330(4) 0.1258(15) Uani 1 1 d . . .
H18A H 1.2165 0.2011 0.0656 0.189 Uiso 1 1 calc R . .
H18B H 1.2222 0.1596 0.1593 0.189 Uiso 1 1 calc R . .
H18C H 1.3236 0.2265 0.1527 0.189 Uiso 1 1 calc R . .
C19 C 0.8390(4) 0.18237(15) 0.0863(2) 0.0693(9) Uani 1 1 d . . .
C20 C 0.7009(4) 0.14489(14) 0.1159(2) 0.0644(8) Uani 1 1 d . . .
C21 C 0.5888(4) 0.11736(17) 0.0491(2) 0.0823(10) Uani 1 1 d . . .
H21 H 0.4969 0.0933 0.0678 0.099 Uiso 1 1 calc R . .
C22 C 0.6166(5) 0.1264(2) -0.0445(3) 0.1043(13) Uani 1 1 d . . .
H22 H 0.5432 0.1083 -0.0896 0.125 Uiso 1 1 calc R . .
C23 C 0.7556(6) 0.1629(2) -0.0725(3) 0.1063(14) Uani 1 1 d . . .
H23 H 0.7730 0.1681 -0.1363 0.128 Uiso 1 1 calc R . .
C24 C 0.8650(5) 0.19070(19) -0.0093(3) 0.0913(11) Uani 1 1 d . . .
H24 H 0.9557 0.2149 -0.0292 0.110 Uiso 1 1 calc R . .
C25 C 1.1511(4) 0.0613(2) 0.9007(2) 0.0868(10) Uani 1 1 d . . .
H25 H 1.2065 0.0726 0.9570 0.104 Uiso 1 1 calc R . .
C26 C 1.1417(4) 0.10725(17) 0.8283(2) 0.0709(9) Uani 1 1 d . . .
C27 C 0.5641(4) 0.04416(17) 0.2758(2) 0.0865(10) Uani 1 1 d . . .
H27 H 0.6183 0.0176 0.2328 0.104 Uiso 1 1 calc R . .
C28 C 0.4566(5) 0.01428(19) 0.3368(3) 0.1030(13) Uani 1 1 d . . .
H28 H 0.4393 -0.0320 0.3356 0.124 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.368(4) . ?
O1 C11 1.244(3) . ?
O2 C26 1.344(4) . ?
O2 H2 0.8200 . ?
N1 C19 1.367(4) . ?
N1 C6 1.387(3) . ?
N1 C16 1.471(4) . ?
C1 C2 1.343(5) . ?
C1 C28 1.347(5) . ?
C2 C3 1.376(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C27 1.374(4) . ?
C4 C5 1.472(4) . ?
C5 C6 1.376(4) . ?
C5 C20 1.419(4) . ?
C6 C7 1.446(4) . ?
C7 C8 1.336(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.427(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.329(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.451(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.459(4) . ?
C12 C13 1.397(4) . ?
C12 C26 1.405(4) . ?
C13 C14 1.363(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(5) . ?
C14 H14 0.9300 . ?
C15 C25 1.352(5) . ?
C15 H15 0.9300 . ?
C16 C18 1.416(5) . ?
C16 C17 1.463(5) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C24 1.394(4) . ?
C19 C20 1.419(4) . ?
C20 C21 1.400(4) . ?
C21 C22 1.371(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.408(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.355(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.378(4) . ?
C25 H25 0.9300 . ?
C27 C28 1.385(4) . ?
C27 H27 0.9300 . ?
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
C26 O2 H2 109.5 . . ?
C19 N1 C6 108.4(2) . . ?
C19 N1 C16 125.4(3) . . ?
C6 N1 C16 126.0(3) . . ?
C2 C1 C28 122.7(3) . . ?
C2 C1 F1 118.6(3) . . ?
C28 C1 F1 118.6(4) . . ?
C1 C2 C3 118.1(3) . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 H2A 120.9 . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C27 C4 C3 117.1(3) . . ?
C27 C4 C5 121.6(3) . . ?
C3 C4 C5 121.3(3) . . ?
C6 C5 C20 107.1(2) . . ?
C6 C5 C4 126.5(3) . . ?
C20 C5 C4 126.3(3) . . ?
C5 C6 N1 109.5(3) . . ?
C5 C6 C7 129.1(3) . . ?
N1 C6 C7 121.4(3) . . ?
C8 C7 C6 125.5(3) . . ?
C8 C7 H7 117.2 . . ?
C6 C7 H7 117.2 . . ?
C7 C8 C9 124.1(3) . . ?
C7 C8 H8 117.9 . . ?
C9 C8 H8 117.9 . . ?
C10 C9 C8 124.8(3) . . ?
C10 C9 H9 117.6 . . ?
C8 C9 H9 117.6 . . ?
C9 C10 C11 122.4(3) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
O1 C11 C10 118.7(3) . . ?
O1 C11 C12 119.5(3) . . ?
C10 C11 C12 121.8(3) . . ?
C13 C12 C26 117.4(3) . . ?
C13 C12 C11 122.5(3) . . ?
C26 C12 C11 120.1(3) . . ?
C14 C13 C12 121.6(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 119.3(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.4 . . ?
C25 C15 C14 120.8(3) . . ?
C25 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C18 C16 C17 123.7(3) . . ?
C18 C16 N1 115.4(3) . . ?
C17 C16 N1 113.1(3) . . ?
C18 C16 H16 99.4 . . ?
C17 C16 H16 99.4 . . ?
N1 C16 H16 99.4 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C24 131.7(3) . . ?
N1 C19 C20 108.2(3) . . ?
C24 C19 C20 120.1(4) . . ?
C21 C20 C5 133.3(3) . . ?
C21 C20 C19 119.9(3) . . ?
C5 C20 C19 106.7(3) . . ?
C22 C21 C20 118.9(3) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C21 C22 C23 120.3(4) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 121.9(4) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C23 C24 C19 118.8(4) . . ?
C23 C24 H24 120.6 . . ?
C19 C24 H24 120.6 . . ?
C15 C25 C26 120.5(4) . . ?
C15 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
O2 C26 C25 117.9(3) . . ?
O2 C26 C12 121.9(3) . . ?
C25 C26 C12 120.3(3) . . ?
C4 C27 C28 121.2(3) . . ?
C4 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
C1 C28 C27 118.8(3) . . ?
C1 C28 H28 120.6 . . ?
C27 C28 H28 120.6 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        20.33
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.029
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.058
;
_vrf_THETM01_I                   
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6].
RESPONSE: The crystal was poorly diffracting at higher Bragg angles.
The situation did not improve even after recrystallisation and
fresh data collection.
;
####################################################################### 
# 
# 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_chem_veerendra_i2_54_29_07_0m
_database_code_depnum_ccdc_archive 'CCDC 1048306'

_audit_update_record             
;
2015-02-07 deposited with the CCDC.
2015-04-23 downloaded from the CCDC.
;
_publcif_datablock.id            {f3ec9aae-d1f1-4b25-b032-938f22f35a07}

# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H26 F N O2'
_chemical_formula_sum            'C29 H26 F N O2'
_chemical_formula_weight         439.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6019(2)
_cell_length_b                   11.2740(3)
_cell_length_c                   12.5983(3)
_cell_angle_alpha                92.1180(10)
_cell_angle_beta                 105.2540(10)
_cell_angle_gamma                101.5130(10)
_cell_volume                     1149.81(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8756
_exptl_absorpt_correction_T_max  0.9077
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15526
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         24.68
_reflns_number_total             3888
_reflns_number_gt                3036
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0590P)²+0.1460P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3888
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1125
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.003

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.64327(14) 1.51158(10) 0.36169(9) 0.0832(4) Uani 1 1 d . . .
O1 O 0.33030(16) 0.27847(10) -0.05702(9) 0.0622(3) Uani 1 1 d . . .
O2 O 0.21864(19) 0.81256(12) -0.07156(11) 0.0791(4) Uani 1 1 d . . .
N1 N -0.15761(15) 1.03284(11) 0.33400(10) 0.0466(3) Uani 1 1 d . . .
C1 C 0.4983(2) 1.43527(16) 0.35985(12) 0.0566(4) Uani 1 1 d . . .
C2 C 0.3672(2) 1.48374(15) 0.36491(13) 0.0593(5) Uani 1 1 d . . .
H2 H 0.3761 1.5675 0.3688 0.071 Uiso 1 1 calc R . .
C3 C 0.2209(2) 1.40619(14) 0.36418(13) 0.0533(4) Uani 1 1 d . . .
H3 H 0.1302 1.4383 0.3667 0.064 Uiso 1 1 calc R . .
C4 C 0.20627(19) 1.28099(13) 0.35974(12) 0.0450(4) Uani 1 1 d . . .
C5 C 0.05199(18) 1.19903(13) 0.36363(12) 0.0444(4) Uani 1 1 d . . .
C6 C -0.02270(18) 1.09028(13) 0.29996(12) 0.0443(4) Uani 1 1 d . . .
C7 C 0.03325(19) 1.03973(14) 0.21304(12) 0.0464(4) Uani 1 1 d . . .
H7 H 0.0774 1.0957 0.1705 0.056 Uiso 1 1 calc R . .
C8 C 0.02991(19) 0.92364(14) 0.18588(13) 0.0478(4) Uani 1 1 d . . .
H8 H -0.0193 0.8646 0.2236 0.057 Uiso 1 1 calc R . .
C9 C 0.09801(18) 0.88472(14) 0.10171(13) 0.0482(4) Uani 1 1 d . . .
H9 H 0.1372 0.9437 0.0598 0.058 Uiso 1 1 calc R . .
C10 C 0.1100(2) 0.77118(14) 0.07842(13) 0.0507(4) Uani 1 1 d . . .
H10 H 0.0708 0.7106 0.1189 0.061 Uiso 1 1 calc R . .
C11 C 0.1824(2) 0.73811(15) -0.00849(13) 0.0528(4) Uani 1 1 d . . .
C12 C 0.21368(19) 0.61389(14) -0.01861(12) 0.0483(4) Uani 1 1 d . . .
C13 C 0.2291(2) 0.56739(15) -0.11804(13) 0.0573(4) Uani 1 1 d . . .
H13 H 0.2141 0.6128 -0.1787 0.069 Uiso 1 1 calc R . .
C14 C 0.2662(2) 0.45530(15) -0.12802(13) 0.0585(4) Uani 1 1 d . . .
H14 H 0.2740 0.4248 -0.1956 0.070 Uiso 1 1 calc R . .
C15 C 0.2922(2) 0.38750(14) -0.03837(13) 0.0489(4) Uani 1 1 d . . .
C16 C 0.3641(3) 0.20699(16) 0.03290(15) 0.0689(5) Uani 1 1 d . . .
H16A H 0.4578 0.2511 0.0899 0.103 Uiso 1 1 calc R . .
H16B H 0.3876 0.1326 0.0082 0.103 Uiso 1 1 calc R . .
H16C H 0.2699 0.1888 0.0615 0.103 Uiso 1 1 calc R . .
C17 C 0.4909(2) 1.31335(16) 0.35472(13) 0.0572(4) Uani 1 1 d . . .
H17 H 0.5822 1.2826 0.3510 0.069 Uiso 1 1 calc R . .
C18 C 0.3443(2) 1.23639(15) 0.35525(13) 0.0520(4) Uani 1 1 d . . .
H18 H 0.3377 1.1529 0.3525 0.062 Uiso 1 1 calc R . .
C19 C -0.16850(19) 1.10639(14) 0.42139(12) 0.0470(4) Uani 1 1 d . . .
C20 C -0.04014(18) 1.21100(13) 0.44136(12) 0.0455(4) Uani 1 1 d . . .
C21 C -0.0214(2) 1.29780(15) 0.52893(13) 0.0536(4) Uani 1 1 d . . .
H21 H 0.0626 1.3674 0.5434 0.064 Uiso 1 1 calc R . .
C22 C -0.1289(2) 1.27852(17) 0.59295(14) 0.0604(5) Uani 1 1 d . . .
H22 H -0.1175 1.3358 0.6511 0.072 Uiso 1 1 calc R . .
C23 C -0.2548(2) 1.17473(17) 0.57249(15) 0.0625(5) Uani 1 1 d . . .
H23 H -0.3255 1.1638 0.6176 0.075 Uiso 1 1 calc R . .
C24 C -0.2771(2) 1.08813(16) 0.48734(14) 0.0570(4) Uani 1 1 d . . .
H24 H -0.3620 1.0192 0.4739 0.068 Uiso 1 1 calc R . .
C25 C -0.29591(18) 0.93907(14) 0.26456(13) 0.0490(4) Uani 1 1 d . . .
H25 H -0.2610 0.9149 0.2005 0.059 Uiso 1 1 calc R . .
C26 C -0.3302(2) 0.82555(15) 0.32283(17) 0.0686(5) Uani 1 1 d . . .
H26A H -0.2318 0.7941 0.3449 0.103 Uiso 1 1 calc R . .
H26B H -0.4164 0.7654 0.2735 0.103 Uiso 1 1 calc R . .
H26C H -0.3639 0.8452 0.3870 0.103 Uiso 1 1 calc R . .
C27 C -0.4468(2) 0.99102(17) 0.22009(16) 0.0663(5) Uani 1 1 d . . .
H27A H -0.4917 1.0089 0.2795 0.099 Uiso 1 1 calc R . .
H27B H -0.5281 0.9328 0.1656 0.099 Uiso 1 1 calc R . .
H27C H -0.4164 1.0643 0.1870 0.099 Uiso 1 1 calc R . .
C28 C 0.2761(2) 0.43135(15) 0.06077(13) 0.0551(4) Uani 1 1 d . . .
H28 H 0.2922 0.3861 0.1215 0.066 Uiso 1 1 calc R . .
C29 C 0.2358(2) 0.54340(15) 0.06902(13) 0.0557(4) Uani 1 1 d . . .
H29 H 0.2232 0.5721 0.1357 0.067 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.3603(19) . ?
O1 C15 1.3616(18) . ?
O1 C16 1.416(2) . ?
O2 C11 1.228(2) . ?
N1 C6 1.3901(19) . ?
N1 C19 1.3880(19) . ?
N1 C25 1.4765(19) . ?
C1 C17 1.362(2) . ?
C1 C2 1.363(3) . ?
C2 C3 1.379(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(2) . ?
C3 H3 0.9300 . ?
C4 C18 1.392(2) . ?
C4 C5 1.472(2) . ?
C5 C6 1.379(2) . ?
C5 C20 1.431(2) . ?
C6 C7 1.448(2) . ?
C7 C8 1.333(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.434(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.333(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.466(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.485(2) . ?
C12 C29 1.379(2) . ?
C12 C13 1.389(2) . ?
C13 C14 1.373(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(2) . ?
C14 H14 0.9300 . ?
C15 C28 1.377(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.383(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.396(2) . ?
C19 C20 1.409(2) . ?
C20 C21 1.402(2) . ?
C21 C22 1.370(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.390(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(2) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C27 1.512(2) . ?
C25 C26 1.515(2) . ?
C25 H25 0.9800 . ?
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 C29 1.382(2) . ?
C28 H28 0.9300 . ?
C29 H29 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
C15 O1 C16 118.12(13) . . ?
C6 N1 C19 107.61(12) . . ?
C6 N1 C25 124.22(12) . . ?
C19 N1 C25 124.42(13) . . ?
F1 C1 C17 118.56(18) . . ?
F1 C1 C2 118.83(17) . . ?
C17 C1 C2 122.60(16) . . ?
C1 C2 C3 118.70(17) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 121.28(17) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C18 117.64(15) . . ?
C3 C4 C5 121.02(15) . . ?
C18 C4 C5 121.30(14) . . ?
C6 C5 C20 106.85(13) . . ?
C6 C5 C4 126.47(14) . . ?
C20 C5 C4 126.42(13) . . ?
C5 C6 N1 110.03(13) . . ?
C5 C6 C7 125.61(14) . . ?
N1 C6 C7 124.32(13) . . ?
C8 C7 C6 128.59(15) . . ?
C8 C7 H7 115.7 . . ?
C6 C7 H7 115.7 . . ?
C7 C8 C9 123.63(15) . . ?
C7 C8 H8 118.2 . . ?
C9 C8 H8 118.2 . . ?
C10 C9 C8 125.55(15) . . ?
C10 C9 H9 117.2 . . ?
C8 C9 H9 117.2 . . ?
C9 C10 C11 122.57(15) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
O2 C11 C10 120.49(15) . . ?
O2 C11 C12 120.25(15) . . ?
C10 C11 C12 119.25(14) . . ?
C29 C12 C13 117.75(15) . . ?
C29 C12 C11 122.52(14) . . ?
C13 C12 C11 119.66(14) . . ?
C14 C13 C12 120.86(15) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.47(15) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
O1 C15 C28 124.73(14) . . ?
O1 C15 C14 115.61(14) . . ?
C28 C15 C14 119.65(15) . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 C17 C18 118.28(17) . . ?
C1 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C17 C18 C4 121.49(16) . . ?
C17 C18 H18 119.3 . . ?
C4 C18 H18 119.3 . . ?
N1 C19 C24 130.42(15) . . ?
N1 C19 C20 108.52(13) . . ?
C24 C19 C20 121.01(15) . . ?
C21 C20 C19 119.33(14) . . ?
C21 C20 C5 133.61(15) . . ?
C19 C20 C5 106.98(13) . . ?
C22 C21 C20 118.96(16) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C21 C22 C23 121.11(16) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C24 C23 C22 121.52(16) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C19 118.07(16) . . ?
C23 C24 H24 121.0 . . ?
C19 C24 H24 121.0 . . ?
N1 C25 C27 111.08(13) . . ?
N1 C25 C26 112.17(14) . . ?
C27 C25 C26 113.42(14) . . ?
N1 C25 H25 106.6 . . ?
C27 C25 H25 106.5 . . ?
C26 C25 H25 106.6 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C15 C28 C29 119.21(15) . . ?
C15 C28 H28 120.4 . . ?
C29 C28 H28 120.4 . . ?
C12 C29 C28 122.03(15) . . ?
C12 C29 H29 119.0 . . ?
C28 C29 H29 119.0 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.68
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.032
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.035
;

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
####################################################################### 
# 
# 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_chem_veerendra_i2_55_0ma
_database_code_depnum_ccdc_archive 'CCDC 1048307'

_audit_update_record             
;
2015-02-07 deposited with the CCDC.
2015-04-23 downloaded from the CCDC.
;
_publcif_datablock.id            {3136eb96-ff05-40a7-8ef8-242e4515441e}

# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H23 Cl F N O'
_chemical_formula_sum            'C28 H23 Cl F N O'
_chemical_formula_weight         443.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5512(5)
_cell_length_b                   11.0250(7)
_cell_length_c                   12.6098(5)
_cell_angle_alpha                88.967(3)
_cell_angle_beta                 76.327(2)
_cell_angle_gamma                78.699(2)
_cell_volume                     1132.23(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8777
_exptl_absorpt_correction_T_max  0.9017
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20370
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         28.34
_reflns_number_total             5594
_reflns_number_gt                3986
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0670P)²+0.1871P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5594
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.003

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.34370(7) 0.76459(4) 1.00725(5) 0.07334(19) Uani 1 1 d . . .
F1 F 0.65641(14) -0.52070(11) 0.64468(10) 0.0745(4) Uani 1 1 d . . .
O1 O 0.2295(2) 0.18499(13) 1.07000(12) 0.0760(4) Uani 1 1 d . . .
N1 N -0.15320(15) -0.04248(12) 0.67233(11) 0.0427(3) Uani 1 1 d . . .
C1 C 0.2919(2) 0.61962(16) 1.00794(15) 0.0516(4) Uani 1 1 d . . .
C2 C 0.2555(2) 0.57871(17) 0.91700(15) 0.0584(5) Uani 1 1 d . . .
H2 H 0.2558 0.6284 0.8566 0.070 Uiso 1 1 calc R . .
C3 C 0.2181(2) 0.46242(17) 0.91591(14) 0.0551(4) Uani 1 1 d . . .
H3 H 0.1924 0.4344 0.8542 0.066 Uiso 1 1 calc R . .
C4 C 0.21827(19) 0.38690(15) 1.00442(13) 0.0450(4) Uani 1 1 d . . .
C5 C 0.1894(2) 0.25752(16) 1.00282(14) 0.0490(4) Uani 1 1 d . . .
C6 C 0.1154(2) 0.21962(15) 0.91827(14) 0.0466(4) Uani 1 1 d . . .
H6 H 0.0698 0.2803 0.8762 0.056 Uiso 1 1 calc R . .
C7 C 0.11044(18) 0.10152(15) 0.89889(13) 0.0435(4) Uani 1 1 d . . .
H7 H 0.1550 0.0414 0.9419 0.052 Uiso 1 1 calc R . .
C8 C 0.04092(19) 0.06226(15) 0.81614(13) 0.0434(4) Uani 1 1 d . . .
H8 H -0.0130 0.1229 0.7779 0.052 Uiso 1 1 calc R . .
C9 C 0.04830(18) -0.05631(14) 0.79007(13) 0.0418(3) Uani 1 1 d . . .
H9 H 0.0981 -0.1155 0.8316 0.050 Uiso 1 1 calc R . .
C10 C -0.01301(18) -0.10220(14) 0.70423(13) 0.0401(3) Uani 1 1 d . . .
C11 C 0.06055(18) -0.20637(14) 0.63792(13) 0.0404(3) Uani 1 1 d . . .
C12 C 0.21764(19) -0.28880(14) 0.63962(12) 0.0402(3) Uani 1 1 d . . .
C13 C 0.2355(2) -0.41698(15) 0.62992(14) 0.0475(4) Uani 1 1 d . . .
H13 H 0.1467 -0.4504 0.6225 0.057 Uiso 1 1 calc R . .
C14 C 0.3828(2) -0.49504(15) 0.63112(14) 0.0524(4) Uani 1 1 d . . .
H14 H 0.3940 -0.5803 0.6243 0.063 Uiso 1 1 calc R . .
C15 C 0.5115(2) -0.44440(16) 0.64254(14) 0.0508(4) Uani 1 1 d . . .
C16 C 0.2894(3) 0.54899(18) 1.09834(17) 0.0643(5) Uani 1 1 d . . .
H16 H 0.3112 0.5791 1.1606 0.077 Uiso 1 1 calc R . .
C17 C 0.2539(3) 0.43209(18) 1.09593(16) 0.0607(5) Uani 1 1 d . . .
H17 H 0.2539 0.3830 1.1567 0.073 Uiso 1 1 calc R . .
C18 C -0.03751(19) -0.21170(14) 0.56137(13) 0.0415(3) Uani 1 1 d . . .
C19 C -0.16768(19) -0.10816(14) 0.58374(13) 0.0429(4) Uani 1 1 d . . .
C20 C -0.2807(2) -0.08326(17) 0.51870(15) 0.0527(4) Uani 1 1 d . . .
H20 H -0.3658 -0.0144 0.5331 0.063 Uiso 1 1 calc R . .
C21 C -0.2626(2) -0.16345(18) 0.43279(15) 0.0579(5) Uani 1 1 d . . .
H21 H -0.3366 -0.1481 0.3884 0.069 Uiso 1 1 calc R . .
C22 C -0.1361(2) -0.26734(18) 0.41027(15) 0.0553(4) Uani 1 1 d . . .
H22 H -0.1278 -0.3204 0.3518 0.066 Uiso 1 1 calc R . .
C23 C -0.0238(2) -0.29201(16) 0.47347(14) 0.0489(4) Uani 1 1 d . . .
H23 H 0.0604 -0.3614 0.4581 0.059 Uiso 1 1 calc R . .
C24 C -0.28934(18) 0.04552(14) 0.74266(14) 0.0457(4) Uani 1 1 d . . .
H24 H -0.2534 0.0608 0.8086 0.055 Uiso 1 1 calc R . .
C25 C -0.4422(2) -0.00878(17) 0.77949(16) 0.0570(5) Uani 1 1 d . . .
H25A H -0.4906 -0.0142 0.7188 0.086 Uiso 1 1 calc R . .
H25B H -0.5194 0.0434 0.8363 0.086 Uiso 1 1 calc R . .
H25C H -0.4135 -0.0899 0.8068 0.086 Uiso 1 1 calc R . .
C26 C -0.3222(2) 0.16967(16) 0.68936(19) 0.0642(5) Uani 1 1 d . . .
H26A H -0.2246 0.2040 0.6742 0.096 Uiso 1 1 calc R . .
H26B H -0.4094 0.2250 0.7378 0.096 Uiso 1 1 calc R . .
H26C H -0.3533 0.1584 0.6224 0.096 Uiso 1 1 calc R . .
C27 C 0.35363(19) -0.24235(15) 0.64861(14) 0.0464(4) Uani 1 1 d . . .
H27 H 0.3451 -0.1571 0.6533 0.056 Uiso 1 1 calc R . .
C28 C 0.5016(2) -0.31916(17) 0.65077(15) 0.0515(4) Uani 1 1 d . . .
H28 H 0.5915 -0.2869 0.6576 0.062 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7394(18) . ?
F1 C15 1.3605(18) . ?
O1 C5 1.217(2) . ?
N1 C19 1.385(2) . ?
N1 C10 1.3934(19) . ?
N1 C24 1.478(2) . ?
C1 C2 1.363(3) . ?
C1 C16 1.367(3) . ?
C2 C3 1.382(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(2) . ?
C3 H3 0.9300 . ?
C4 C17 1.385(2) . ?
C4 C5 1.496(2) . ?
C5 C6 1.466(2) . ?
C6 C7 1.340(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.428(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.340(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.447(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(2) . ?
C11 C18 1.429(2) . ?
C11 C12 1.472(2) . ?
C12 C27 1.388(2) . ?
C12 C13 1.396(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(3) . ?
C14 H14 0.9300 . ?
C15 C28 1.371(2) . ?
C16 C17 1.383(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.400(2) . ?
C18 C19 1.410(2) . ?
C19 C20 1.395(2) . ?
C20 C21 1.371(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.394(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.372(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.514(2) . ?
C24 C26 1.520(2) . ?
C24 H24 0.9800 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.384(2) . ?
C27 H27 0.9300 . ?
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
C19 N1 C10 107.98(12) . . ?
C19 N1 C24 124.44(13) . . ?
C10 N1 C24 124.38(13) . . ?
C2 C1 C16 121.40(17) . . ?
C2 C1 Cl1 118.68(15) . . ?
C16 C1 Cl1 119.92(14) . . ?
C1 C2 C3 119.04(17) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 121.40(16) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C17 117.98(16) . . ?
C3 C4 C5 122.56(15) . . ?
C17 C4 C5 119.40(16) . . ?
O1 C5 C6 121.02(16) . . ?
O1 C5 C4 119.95(15) . . ?
C6 C5 C4 119.02(15) . . ?
C7 C6 C5 123.02(16) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C6 C7 C8 124.01(16) . . ?
C6 C7 H7 118.0 . . ?
C8 C7 H7 118.0 . . ?
C9 C8 C7 124.23(15) . . ?
C9 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
C8 C9 C10 126.95(15) . . ?
C8 C9 H9 116.5 . . ?
C10 C9 H9 116.5 . . ?
C11 C10 N1 109.61(14) . . ?
C11 C10 C9 126.25(14) . . ?
N1 C10 C9 124.06(13) . . ?
C10 C11 C18 106.80(13) . . ?
C10 C11 C12 126.34(14) . . ?
C18 C11 C12 126.63(14) . . ?
C27 C12 C13 117.72(15) . . ?
C27 C12 C11 121.51(14) . . ?
C13 C12 C11 120.76(14) . . ?
C14 C13 C12 121.11(16) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 118.67(16) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
F1 C15 C14 118.98(16) . . ?
F1 C15 C28 118.32(17) . . ?
C14 C15 C28 122.70(15) . . ?
C1 C16 C17 119.10(17) . . ?
C1 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C4 C17 C16 121.05(18) . . ?
C4 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C23 C18 C19 119.18(15) . . ?
C23 C18 C11 133.52(15) . . ?
C19 C18 C11 107.24(13) . . ?
N1 C19 C20 130.42(15) . . ?
N1 C19 C18 108.36(13) . . ?
C20 C19 C18 121.17(15) . . ?
C21 C20 C19 117.97(17) . . ?
C21 C20 H20 121.0 . . ?
C19 C20 H20 121.0 . . ?
C20 C21 C22 121.73(17) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C23 C22 C21 120.63(17) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C18 119.30(16) . . ?
C22 C23 H23 120.4 . . ?
C18 C23 H23 120.3 . . ?
N1 C24 C25 111.99(13) . . ?
N1 C24 C26 111.68(15) . . ?
C25 C24 C26 112.66(14) . . ?
N1 C24 H24 106.7 . . ?
C25 C24 H24 106.7 . . ?
C26 C24 H24 106.7 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C12 121.91(16) . . ?
C28 C27 H27 119.0 . . ?
C12 C27 H27 119.0 . . ?
C15 C28 C27 117.87(17) . . ?
C15 C28 H28 121.1 . . ?
C27 C28 H28 121.1 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.036
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.047
;

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
