# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_TRY2_a
_database_code_depnum_ccdc_archive 'CCDC 1453038'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;
_audit_creation_date             2016-02-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         '0.11(C25 H15 F2 N O)'
_chemical_formula_sum            'C2.778 H1.667 F0.222 N0.111 O0.111'
_chemical_formula_weight         42.60
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   9.3775(7)
_cell_length_b                   11.0241(8)
_cell_length_c                   9.5231(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.422(4)
_cell_angle_gamma                90
_cell_volume                     922.61(11)
_cell_formula_units_Z            18
_exptl_absorpt_coefficient_mu    0.098
_exptl_crystal_density_diffrn    1.3800
_exptl_crystal_F_000             396.2251
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1243
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         22.97
_diffrn_reflns_theta_min         2.28
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9156
_diffrn_measured_fraction_theta_max 0.9156
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                1143
_reflns_number_total             1237
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.5169
_refine_diff_density_min         -0.2716
_refine_diff_density_rms         0.0527
_refine_ls_d_res_high            0.9105
_refine_ls_d_res_low             8.9246
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.1402
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     262
_refine_ls_number_reflns         1237
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0603
_refine_ls_restrained_S_all      1.1164
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1292P)²+0.2633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.1797
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C14 \\sim C15 \\sim C16 \\sim C17: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(C17) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C14)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C25(H25), C10(H10), C21(H21), C11(H11), C24(H24), C22(H22), C3(H3),
 C4(H4), C6(H6), C5(H5), C16(H16), C17(H17), C15(H15), C14(H14)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
O2 O 0.7914(6) 1.1072(4) 0.4762(6) 0.0742(14) Uani 1.000000 . U
N1 N 0.5954(5) 0.8173(5) 0.6180(5) 0.0563(13) Uani 1.000000 . U
F2 F 1.3380(6) 0.9795(6) 0.2739(7) 0.119(2) Uani 1.000000 . U
C20 C 0.9661(6) 0.9917(6) 0.4040(5) 0.0513(14) Uani 1.000000 . U
C19 C 0.8366(7) 1.0055(6) 0.4598(6) 0.0521(14) Uani 1.000000 . U
C1 C 0.5521(7) 0.8385(6) 0.7419(6) 0.0565(16) Uani 1.000000 . U
C7 C 0.7429(7) 0.9726(5) 0.7486(6) 0.0539(15) Uani 1.000000 . U
C13 C 0.8679(8) 1.0573(6) 0.8067(6) 0.0591(17) Uani 1.000000 . U
C8 C 0.7085(6) 0.9016(5) 0.6188(6) 0.0525(14) Uani 1.000000 . U
C12 C 0.5486(7) 0.7267(7) 0.5127(8) 0.0669(18) Uani 1.000000 . U
H12 H 0.4751(7) 0.6715(7) 0.5167(8) 0.080(2) Uiso 1.000000 R .
C9 C 0.7603(7) 0.8967(6) 0.4951(6) 0.0525(14) Uani 1.000000 . U
C25 C 0.9965(8) 1.0873(6) 0.3224(7) 0.0621(17) Uani 1.000000 . U
H25 H 0.9333(8) 1.1549(6) 0.2994(7) 0.074(2) Uiso 1.000000 R .
C10 C 0.7139(7) 0.8053(6) 0.3937(7) 0.0646(17) Uani 1.000000 . U
H10 H 0.7521(7) 0.8003(6) 0.3159(7) 0.078(2) Uiso 1.000000 R .
C21 C 1.0632(7) 0.8947(6) 0.4416(6) 0.0598(16) Uani 1.000000 . U
H21 H 1.0435(7) 0.8308(6) 0.4960(6) 0.072(2) Uiso 1.000000 R .
C2 C 0.6421(7) 0.9344(6) 0.8233(6) 0.0582(16) Uani 1.000000 . U
C11 C 0.6085(8) 0.7177(6) 0.4047(8) 0.0710(19) Uani 1.000000 . U
H11 H 0.5807(8) 0.6538(6) 0.3368(8) 0.085(2) Uiso 1.000000 R .
C24 C 1.1197(8) 1.0815(7) 0.2761(8) 0.073(2) Uani 1.000000 . U
H24 H 1.1381(8) 1.1426(7) 0.2172(8) 0.087(2) Uiso 1.000000 R .
C22 C 1.1870(8) 0.8907(7) 0.4007(7) 0.0694(18) Uani 1.000000 . U
H22 H 1.2534(8) 0.8251(7) 0.4279(7) 0.083(2) Uiso 1.000000 R .
C23 C 1.2140(8) 0.9842(7) 0.3186(8) 0.0699(19) Uani 1.000000 . U
C3 C 0.6186(8) 0.9718(7) 0.9556(7) 0.072(2) Uani 1.000000 . U
H3 H 0.6756(8) 1.0353(7) 1.0121(7) 0.086(2) Uiso 1.000000 R .
C4 C 0.5142(10) 0.9160(9) 1.0002(9) 0.085(2) Uani 1.000000 . U
H4 H 0.4985(10) 0.9416(9) 1.0868(9) 0.102(3) Uiso 1.000000 R .
C6 C 0.4445(8) 0.7814(8) 0.7891(8) 0.080(2) Uani 1.000000 . U
H6 H 0.3847(8) 0.7185(8) 0.7341(8) 0.097(3) Uiso 1.000000 R .
C5 C 0.4302(9) 0.8206(10) 0.9177(8) 0.089(2) Uani 1.000000 . U
H5 H 0.3608(9) 0.7818(10) 0.9524(8) 0.106(3) Uiso 1.000000 R .
C18 C 1.0173(10) 1.0267(8) 0.8153(7) 0.076(2) Uani 1.000000 . U
C16 C 1.1261(17) 1.2073(12) 0.9222(11) 0.127(4) Uani 1.000000 . U
H16 H 1.2106(17) 1.2575(12) 0.9606(11) 0.152(5) Uiso 1.000000 R .
C17 C 1.1420(11) 1.1000(11) 0.8709(9) 0.107(3) Uani 1.000000 . U
H17 H 1.2368(11) 1.0740(11) 0.8723(9) 0.128(4) Uiso 1.000000 R .
C15 C 0.9831(18) 1.2479(9) 0.9202(8) 0.125(4) Uani 1.000000 . U
H15 H 0.9793(18) 1.3251(9) 0.9583(8) 0.151(5) Uiso 1.000000 R .
F1 F 1.0393(6) 0.9238(6) 0.7665(6) 0.118(2) Uani 1.000000 . U
C14 C 0.8338(14) 1.1778(7) 0.8618(6) 0.124(4) Uani 1.000000 . U
H14 H 0.7393(14) 1.2046(7) 0.8604(6) 0.149(5) Uiso 1.000000 R .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C19 1.227(8) . ?
N1 C1 1.395(7) . ?
N1 C8 1.407(8) . ?
N1 C12 1.375(8) . ?
F2 C23 1.371(8) . ?
C20 C19 1.494(8) . ?
C20 C25 1.396(8) . ?
C20 C21 1.368(9) . ?
C19 C9 1.493(9) . ?
C1 C2 1.406(9) . ?
C1 C6 1.390(9) . ?
C7 C13 1.448(9) . ?
C7 C8 1.402(8) . ?
C7 C2 1.431(8) . ?
C13 C18 1.416(10) . ?
C13 C14 1.503(12) . ?
C8 C9 1.424(8) . ?
C12 C11 1.337(9) . ?
C9 C10 1.358(9) . ?
C25 C24 1.375(9) . ?
C10 C11 1.412(10) . ?
C21 C22 1.348(8) . ?
C2 C3 1.414(8) . ?
C24 C23 1.359(10) . ?
C22 C23 1.369(10) . ?
C3 C4 1.344(11) . ?
C4 C5 1.383(13) . ?
C6 C5 1.349(11) . ?
C18 C17 1.367(12) . ?
C18 F1 1.270(10) . ?
C16 C17 1.307(18) . ?
C16 C15 1.408(17) . ?
C15 C14 1.524(16) . ?

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
C8 N1 C1 109.0(5) . . ?
C12 N1 C1 128.7(5) . . ?
C12 N1 C8 122.1(5) . . ?
C25 C20 C19 118.0(5) . . ?
C21 C20 C19 122.4(5) . . ?
C21 C20 C25 119.3(5) . . ?
C20 C19 O2 119.8(5) . . ?
C9 C19 O2 119.4(5) . . ?
C9 C19 C20 120.7(5) . . ?
C2 C1 N1 107.3(5) . . ?
C6 C1 N1 131.0(6) . . ?
C6 C1 C2 121.7(6) . . ?
C8 C7 C13 127.1(5) . . ?
C2 C7 C13 125.9(5) . . ?
C2 C7 C8 106.5(5) . . ?
C18 C13 C7 121.4(6) . . ?
C14 C13 C7 117.5(7) . . ?
C14 C13 C18 121.1(7) . . ?
C7 C8 N1 108.4(5) . . ?
C9 C8 N1 116.4(5) . . ?
C9 C8 C7 135.2(6) . . ?
C11 C12 N1 120.1(6) . . ?
C8 C9 C19 119.0(5) . . ?
C10 C9 C19 119.7(5) . . ?
C10 C9 C8 119.9(6) . . ?
C24 C25 C20 120.1(6) . . ?
C11 C10 C9 120.9(6) . . ?
C22 C21 C20 120.7(6) . . ?
C7 C2 C1 108.7(5) . . ?
C3 C2 C1 117.4(6) . . ?
C3 C2 C7 133.9(6) . . ?
C10 C11 C12 120.0(6) . . ?
C23 C24 C25 118.2(6) . . ?
C23 C22 C21 119.4(7) . . ?
C24 C23 F2 118.1(7) . . ?
C22 C23 F2 119.7(7) . . ?
C22 C23 C24 122.2(6) . . ?
C4 C3 C2 120.3(7) . . ?
C5 C4 C3 120.2(7) . . ?
C5 C6 C1 117.5(8) . . ?
C6 C5 C4 122.8(7) . . ?
C17 C18 C13 125.3(9) . . ?
F1 C18 C13 118.4(7) . . ?
F1 C18 C17 116.3(9) . . ?
C15 C16 C17 121.0(10) . . ?
C16 C17 C18 119.1(12) . . ?
C14 C15 C16 126.3(10) . . ?
C15 C14 C13 107.2(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
C16 0.1000
C17 0.1000
C15 0.1000
C14 0.1000

loop_
_restr_U_similar_atom_site_label_1
_restr_U_similar_atom_site_label_2
_restr_U_similar_weight_param
C16 C17 0.0400
C16 C15 0.0400
C15 C14 0.0400

_chemical_name_systematic        
(4-fluorophenyl)(10-(2-fluorophenyl)pyrido[1,2-a]indol-9-yl)methanone
_chemical_name_common            pyrido[1,2,a]indole
