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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_h396
_database_code_depnum_ccdc_archive 'CCDC 1584466'
_audit_update_record             
;
2017-11-08 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H37 I N2'
_chemical_formula_sum            'C26 H37 I N2'
_chemical_formula_weight         504.47

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_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                   9.4821(7)
_cell_length_b                   14.8496(8)
_cell_length_c                   17.7290(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.901(2)
_cell_angle_gamma                90
_cell_volume                     2451.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4510
_cell_measurement_theta_min      2.340
_cell_measurement_theta_max      29.574

_exptl_crystal_description       'prism frag'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.463
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.225
_exptl_absorpt_coefficient_mu    1.320
_shelx_estimated_absorpt_T_min   0.580
_shelx_estimated_absorpt_T_max   0.755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.580
_exptl_absorpt_correction_T_max  0.755
_exptl_absorpt_process_details   Sadabs
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37662
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.340
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6892
_reflns_number_gt                6452
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 v2016.9.0'
_computing_cell_refinement       
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2016.9.0'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0302P)²+1.8889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6892
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0222
_refine_ls_wR_factor_ref         0.0621
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
I1 I 0.72679(2) 0.84043(2) 0.11057(2) 0.02018(4) Uani 1 1 d . . . . .
N2 N 0.62759(12) 0.61640(8) 0.30542(6) 0.0131(2) Uani 1 1 d . . . . .
N1 N 0.62042(12) 0.54561(8) 0.18635(6) 0.0118(2) Uani 1 1 d . . . . .
C12 C 0.64313(14) 0.60800(9) 0.38821(7) 0.0124(2) Uani 1 1 d . . . . .
C1 C 0.64372(13) 0.54580(9) 0.26263(7) 0.0122(2) Uani 1 1 d . . . . .
H1 H 0.6743 0.4910 0.2883 0.015 Uiso 1 1 calc R U . . .
C13 C 0.51993(15) 0.61224(10) 0.42071(8) 0.0150(2) Uani 1 1 d . . . . .
C11 C 0.58013(14) 0.40356(9) 0.11482(8) 0.0131(2) Uani 1 1 d . . . . .
C17 C 0.78122(14) 0.60430(9) 0.43339(8) 0.0140(2) Uani 1 1 d . . . . .
C6 C 0.67539(14) 0.47262(9) 0.14583(7) 0.0119(2) Uani 1 1 d . . . . .
C16 C 0.79376(15) 0.60693(10) 0.51314(8) 0.0161(2) Uani 1 1 d . . . . .
H16 H 0.8864 0.6043 0.5448 0.019 Uiso 1 1 calc R U . . .
C7 C 0.81621(14) 0.47876(9) 0.13192(8) 0.0136(2) Uani 1 1 d . . . . .
C15 C 0.67321(16) 0.61341(10) 0.54711(8) 0.0167(3) Uani 1 1 d . . . . .
C2 C 0.53873(15) 0.61451(10) 0.13430(8) 0.0155(2) Uani 1 1 d . . . . .
H2A H 0.4962 0.5853 0.0850 0.019 Uiso 1 1 calc R U . . .
H2B H 0.6064 0.6613 0.1233 0.019 Uiso 1 1 calc R U . . .
C10 C 0.62893(15) 0.33976(9) 0.06770(8) 0.0149(2) Uani 1 1 d . . . . .
H10 H 0.5668 0.2926 0.0457 0.018 Uiso 1 1 calc R U . . .
C14 C 0.53769(16) 0.61443(10) 0.50062(8) 0.0174(3) Uani 1 1 d . . . . .
H14 H 0.4552 0.6167 0.5238 0.021 Uiso 1 1 calc R U . . .
C5 C 0.61929(17) 0.70931(9) 0.27359(8) 0.0175(3) Uani 1 1 d . . . . .
H5A H 0.6933 0.7161 0.2414 0.021 Uiso 1 1 calc R U . . .
H5B H 0.6423 0.7525 0.3167 0.021 Uiso 1 1 calc R U . . .
C18 C 0.92090(15) 0.55155(10) 0.16748(9) 0.0178(3) Uani 1 1 d . . . . .
H18 H 0.8670 0.5954 0.1942 0.021 Uiso 1 1 calc R U . . .
C26 C 0.91330(15) 0.59589(11) 0.39838(9) 0.0192(3) Uani 1 1 d . . . . .
H26A H 0.9983 0.6118 0.4367 0.029 Uiso 1 1 calc R U . . .
H26B H 0.9053 0.6366 0.3543 0.029 Uiso 1 1 calc R U . . .
H26C H 0.9223 0.5337 0.3813 0.029 Uiso 1 1 calc R U . . .
C9 C 0.76769(16) 0.34462(9) 0.05261(8) 0.0156(3) Uani 1 1 d . . . . .
H9 H 0.7993 0.3011 0.0202 0.019 Uiso 1 1 calc R U . . .
C8 C 0.85986(15) 0.41282(10) 0.08484(8) 0.0163(3) Uani 1 1 d . . . . .
H8 H 0.9547 0.4147 0.0747 0.020 Uiso 1 1 calc R U . . .
C21 C 0.43037(15) 0.39583(10) 0.13315(8) 0.0171(3) Uani 1 1 d . . . . .
H21 H 0.4125 0.4509 0.1624 0.020 Uiso 1 1 calc R U . . .
C3 C 0.41912(16) 0.65980(10) 0.16739(9) 0.0192(3) Uani 1 1 d . . . . .
H3A H 0.3686 0.6136 0.1925 0.023 Uiso 1 1 calc R U . . .
H3B H 0.3487 0.6863 0.1248 0.023 Uiso 1 1 calc R U . . .
C4 C 0.47407(17) 0.73370(10) 0.22574(9) 0.0198(3) Uani 1 1 d . . . . .
H4A H 0.4824 0.7909 0.1983 0.024 Uiso 1 1 calc R U . . .
H4B H 0.4041 0.7428 0.2600 0.024 Uiso 1 1 calc R U . . .
C25 C 0.68602(18) 0.62107(12) 0.63308(9) 0.0234(3) Uani 1 1 d . . . . .
H25A H 0.6877 0.6848 0.6477 0.035 Uiso 1 1 calc R U . . .
H25B H 0.7750 0.5920 0.6587 0.035 Uiso 1 1 calc R U . . .
H25C H 0.6037 0.5914 0.6486 0.035 Uiso 1 1 calc R U . . .
C24 C 0.36937(16) 0.61483(12) 0.37413(9) 0.0232(3) Uani 1 1 d . . . . .
H24A H 0.3042 0.5833 0.4020 0.035 Uiso 1 1 calc R U . . .
H24B H 0.3676 0.5853 0.3245 0.035 Uiso 1 1 calc R U . . .
H24C H 0.3385 0.6776 0.3656 0.035 Uiso 1 1 calc R U . . .
C22 C 0.42124(18) 0.31367(13) 0.18470(10) 0.0266(3) Uani 1 1 d . . . . .
H22A H 0.4323 0.2584 0.1561 0.040 Uiso 1 1 calc R U . . .
H22B H 0.3277 0.3132 0.2006 0.040 Uiso 1 1 calc R U . . .
H22C H 0.4979 0.3170 0.2302 0.040 Uiso 1 1 calc R U . . .
C23 C 0.31457(17) 0.39166(14) 0.06047(10) 0.0297(4) Uani 1 1 d . . . . .
H23A H 0.3187 0.4464 0.0301 0.045 Uiso 1 1 calc R U . . .
H23B H 0.2199 0.3870 0.0747 0.045 Uiso 1 1 calc R U . . .
H23C H 0.3309 0.3389 0.0300 0.045 Uiso 1 1 calc R U . . .
C20 C 0.98653(18) 0.60377(12) 0.10802(10) 0.0265(3) Uani 1 1 d . . . . .
H20A H 1.0423 0.5625 0.0820 0.040 Uiso 1 1 calc R U . . .
H20B H 1.0497 0.6512 0.1339 0.040 Uiso 1 1 calc R U . . .
H20C H 0.9096 0.6310 0.0702 0.040 Uiso 1 1 calc R U . . .
C19 C 1.03921(17) 0.50900(13) 0.22822(10) 0.0260(3) Uani 1 1 d . . . . .
H19A H 0.9952 0.4751 0.2652 0.039 Uiso 1 1 calc R U . . .
H19B H 1.1006 0.5565 0.2552 0.039 Uiso 1 1 calc R U . . .
H19C H 1.0972 0.4683 0.2031 0.039 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
N2 C1 1.3199(17) . ?
N2 C12 1.4527(17) . ?
N2 C5 1.4870(18) . ?
N1 C1 1.3285(17) . ?
N1 C6 1.4505(16) . ?
N1 C2 1.4926(17) . ?
C12 C13 1.3983(19) . ?
C12 C17 1.4008(18) . ?
C1 H1 0.9500 . ?
C13 C14 1.3950(19) . ?
C13 C24 1.5086(19) . ?
C11 C10 1.3984(18) . ?
C11 C6 1.4078(18) . ?
C11 C21 1.5199(18) . ?
C17 C16 1.3969(19) . ?
C17 C26 1.5045(19) . ?
C6 C7 1.4059(18) . ?
C16 C15 1.393(2) . ?
C16 H16 0.9500 . ?
C7 C8 1.3991(19) . ?
C7 C18 1.5213(19) . ?
C15 C14 1.389(2) . ?
C15 C25 1.510(2) . ?
C2 C3 1.528(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C10 C9 1.393(2) . ?
C10 H10 0.9500 . ?
C14 H14 0.9500 . ?
C5 C4 1.518(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C18 C20 1.532(2) . ?
C18 C19 1.536(2) . ?
C18 H18 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C9 C8 1.388(2) . ?
C9 H9 0.9500 . ?
C8 H8 0.9500 . ?
C21 C23 1.528(2) . ?
C21 C22 1.537(2) . ?
C21 H21 1.0000 . ?
C3 C4 1.530(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C12 120.79(11) . . ?
C1 N2 C5 121.50(11) . . ?
C12 N2 C5 116.82(11) . . ?
C1 N1 C6 119.97(11) . . ?
C1 N1 C2 126.50(11) . . ?
C6 N1 C2 113.52(10) . . ?
C13 C12 C17 121.98(12) . . ?
C13 C12 N2 118.65(12) . . ?
C17 C12 N2 119.10(12) . . ?
N2 C1 N1 124.87(12) . . ?
N2 C1 H1 117.6 . . ?
N1 C1 H1 117.6 . . ?
C14 C13 C12 118.01(12) . . ?
C14 C13 C24 118.38(13) . . ?
C12 C13 C24 123.61(13) . . ?
C10 C11 C6 117.81(12) . . ?
C10 C11 C21 120.30(12) . . ?
C6 C11 C21 121.87(12) . . ?
C16 C17 C12 117.98(13) . . ?
C16 C17 C26 120.12(12) . . ?
C12 C17 C26 121.90(12) . . ?
C7 C6 C11 122.63(12) . . ?
C7 C6 N1 118.72(12) . . ?
C11 C6 N1 118.27(11) . . ?
C15 C16 C17 121.33(13) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C8 C7 C6 117.20(12) . . ?
C8 C7 C18 120.07(12) . . ?
C6 C7 C18 122.71(12) . . ?
C14 C15 C16 119.14(13) . . ?
C14 C15 C25 119.13(14) . . ?
C16 C15 C25 121.72(13) . . ?
N1 C2 C3 113.61(11) . . ?
N1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
N1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C9 C10 C11 120.72(13) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C15 C14 C13 121.52(13) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
N2 C5 C4 114.24(12) . . ?
N2 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
N2 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C7 C18 C20 113.11(12) . . ?
C7 C18 C19 109.33(13) . . ?
C20 C18 C19 110.65(13) . . ?
C7 C18 H18 107.9 . . ?
C20 C18 H18 107.9 . . ?
C19 C18 H18 107.9 . . ?
C17 C26 H26A 109.5 . . ?
C17 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C17 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C8 C9 C10 120.17(12) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C8 C7 121.46(13) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C11 C21 C23 111.98(12) . . ?
C11 C21 C22 110.31(12) . . ?
C23 C21 C22 110.92(14) . . ?
C11 C21 H21 107.8 . . ?
C23 C21 H21 107.8 . . ?
C22 C21 H21 107.8 . . ?
C2 C3 C4 113.12(13) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 111.32(12) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C15 C25 H25A 109.5 . . ?
C15 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C15 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C13 C24 H24A 109.5 . . ?
C13 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C13 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C1 N2 C12 C13 -107.27(15) . . . . ?
C5 N2 C12 C13 83.39(16) . . . . ?
C1 N2 C12 C17 78.57(17) . . . . ?
C5 N2 C12 C17 -90.78(15) . . . . ?
C12 N2 C1 N1 174.39(12) . . . . ?
C5 N2 C1 N1 -16.8(2) . . . . ?
C6 N1 C1 N2 164.28(12) . . . . ?
C2 N1 C1 N2 -16.5(2) . . . . ?
C17 C12 C13 C14 1.2(2) . . . . ?
N2 C12 C13 C14 -172.81(12) . . . . ?
C17 C12 C13 C24 -179.01(14) . . . . ?
N2 C12 C13 C24 7.0(2) . . . . ?
C13 C12 C17 C16 -1.4(2) . . . . ?
N2 C12 C17 C16 172.60(12) . . . . ?
C13 C12 C17 C26 177.43(13) . . . . ?
N2 C12 C17 C26 -8.6(2) . . . . ?
C10 C11 C6 C7 -0.8(2) . . . . ?
C21 C11 C6 C7 177.44(13) . . . . ?
C10 C11 C6 N1 172.06(12) . . . . ?
C21 C11 C6 N1 -9.73(19) . . . . ?
C1 N1 C6 C7 -86.81(16) . . . . ?
C2 N1 C6 C7 93.87(14) . . . . ?
C1 N1 C6 C11 100.07(15) . . . . ?
C2 N1 C6 C11 -79.24(15) . . . . ?
C12 C17 C16 C15 -0.3(2) . . . . ?
C26 C17 C16 C15 -179.08(13) . . . . ?
C11 C6 C7 C8 0.3(2) . . . . ?
N1 C6 C7 C8 -172.49(12) . . . . ?
C11 C6 C7 C18 -177.94(13) . . . . ?
N1 C6 C7 C18 9.26(19) . . . . ?
C17 C16 C15 C14 2.0(2) . . . . ?
C17 C16 C15 C25 -176.83(14) . . . . ?
C1 N1 C2 C3 -30.07(19) . . . . ?
C6 N1 C2 C3 149.19(12) . . . . ?
C6 C11 C10 C9 0.4(2) . . . . ?
C21 C11 C10 C9 -177.89(13) . . . . ?
C16 C15 C14 C13 -2.2(2) . . . . ?
C25 C15 C14 C13 176.66(14) . . . . ?
C12 C13 C14 C15 0.7(2) . . . . ?
C24 C13 C14 C15 -179.17(14) . . . . ?
C1 N2 C5 C4 78.51(16) . . . . ?
C12 N2 C5 C4 -112.23(13) . . . . ?
C8 C7 C18 C20 54.94(18) . . . . ?
C6 C7 C18 C20 -126.85(15) . . . . ?
C8 C7 C18 C19 -68.84(17) . . . . ?
C6 C7 C18 C19 109.37(15) . . . . ?
C11 C10 C9 C8 0.5(2) . . . . ?
C10 C9 C8 C7 -1.0(2) . . . . ?
C6 C7 C8 C9 0.6(2) . . . . ?
C18 C7 C8 C9 178.88(13) . . . . ?
C10 C11 C21 C23 -55.47(19) . . . . ?
C6 C11 C21 C23 126.36(15) . . . . ?
C10 C11 C21 C22 68.59(17) . . . . ?
C6 C11 C21 C22 -109.58(15) . . . . ?
N1 C2 C3 C4 79.45(15) . . . . ?
N2 C5 C4 C3 -47.74(17) . . . . ?
C2 C3 C4 C5 -35.92(17) . . . . ?

_refine_diff_density_max         1.366
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_H262
_database_code_depnum_ccdc_archive 'CCDC 1584467'
_audit_update_record             
;
2017-11-08 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H31 B F4 N2'
_chemical_formula_weight         422.31

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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

_cell_length_a                   15.5061(6)
_cell_length_b                   15.3089(8)
_cell_length_c                   9.2595(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.915(2)
_cell_angle_gamma                90
_cell_volume                     2197.75(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7043
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      29.40

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6669
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26959
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.571
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5455
_reflns_number_gt                4071
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+1.5550P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5455
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.33543(8) 0.56768(9) 0.07383(15) 0.0105(3) Uani 1 1 d . . . . .
N2 N 0.18403(8) 0.58113(9) 0.07276(15) 0.0109(3) Uani 1 1 d . . . . .
C1 C 0.26231(10) 0.59926(11) 0.12173(17) 0.0103(3) Uani 1 1 d . . . . .
H1 H 0.2664 0.6394 0.1998 0.012 Uiso 1 1 calc R U . . .
C2 C 0.34439(11) 0.49053(12) -0.02316(19) 0.0145(3) Uani 1 1 d . . . . .
H2A H 0.4016 0.4634 -0.0063 0.017 Uiso 1 1 calc R U . . .
H2B H 0.3413 0.5102 -0.1250 0.017 Uiso 1 1 calc R U . . .
C3 C 0.27451(11) 0.42266(12) 0.00167(19) 0.0152(4) Uani 1 1 d . . . . .
H3A H 0.2636 0.4185 0.1065 0.018 Uiso 1 1 calc R U . . .
H3B H 0.2954 0.3650 -0.0311 0.018 Uiso 1 1 calc R U . . .
C4 C 0.18966(11) 0.44391(12) -0.07768(19) 0.0152(4) Uani 1 1 d . . . . .
H4A H 0.1936 0.4252 -0.1797 0.018 Uiso 1 1 calc R U . . .
H4B H 0.1421 0.4108 -0.0330 0.018 Uiso 1 1 calc R U . . .
C5 C 0.16940(11) 0.54102(12) -0.07221(18) 0.0142(4) Uani 1 1 d . . . . .
H5A H 0.2057 0.5717 -0.1431 0.017 Uiso 1 1 calc R U . . .
H5B H 0.1084 0.5499 -0.1016 0.017 Uiso 1 1 calc R U . . .
C6 C 0.41448(10) 0.61203(11) 0.11752(18) 0.0118(3) Uani 1 1 d . . . . .
C7 C 0.43470(11) 0.69063(12) 0.04938(18) 0.0142(3) Uani 1 1 d . . . . .
C8 C 0.50988(11) 0.73331(12) 0.09441(19) 0.0159(4) Uani 1 1 d . . . . .
H8 H 0.5248 0.7871 0.0502 0.019 Uiso 1 1 calc R U . . .
C9 C 0.56359(11) 0.69949(12) 0.20184(19) 0.0160(4) Uani 1 1 d . . . . .
C10 C 0.54243(11) 0.61955(12) 0.26414(19) 0.0147(4) Uani 1 1 d . . . . .
H10 H 0.5795 0.5955 0.3365 0.018 Uiso 1 1 calc R U . . .
C11 C 0.46819(10) 0.57402(11) 0.22285(18) 0.0130(3) Uani 1 1 d . . . . .
C12 C 0.37860(12) 0.72992(13) -0.0688(2) 0.0211(4) Uani 1 1 d . . . . .
H12A H 0.4148 0.7624 -0.1361 0.032 Uiso 1 1 calc R U . . .
H12B H 0.3366 0.7697 -0.0260 0.032 Uiso 1 1 calc R U . . .
H12C H 0.3481 0.6832 -0.1209 0.032 Uiso 1 1 calc R U . . .
C13 C 0.64239(12) 0.74908(13) 0.2537(2) 0.0226(4) Uani 1 1 d . . . . .
H13A H 0.6676 0.7805 0.1723 0.034 Uiso 1 1 calc R U . . .
H13B H 0.6848 0.7080 0.2940 0.034 Uiso 1 1 calc R U . . .
H13C H 0.6258 0.7910 0.3283 0.034 Uiso 1 1 calc R U . . .
C14 C 0.44880(12) 0.48680(12) 0.2909(2) 0.0190(4) Uani 1 1 d . . . . .
H14A H 0.4654 0.4398 0.2250 0.028 Uiso 1 1 calc R U . . .
H14B H 0.3869 0.4828 0.3099 0.028 Uiso 1 1 calc R U . . .
H14C H 0.4815 0.4812 0.3819 0.028 Uiso 1 1 calc R U . . .
C15 C 0.11041(10) 0.61853(11) 0.14613(18) 0.0118(3) Uani 1 1 d . . . . .
C16 C 0.08987(11) 0.70613(12) 0.1201(2) 0.0155(4) Uani 1 1 d . . . . .
C17 C 0.01726(11) 0.74000(12) 0.1868(2) 0.0203(4) Uani 1 1 d . . . . .
H17 H 0.0020 0.7993 0.1705 0.024 Uiso 1 1 calc R U . . .
C18 C -0.03348(11) 0.68932(13) 0.2765(2) 0.0192(4) Uani 1 1 d . . . . .
C19 C -0.01056(11) 0.60274(12) 0.30017(19) 0.0169(4) Uani 1 1 d . . . . .
H19 H -0.0449 0.5679 0.3617 0.020 Uiso 1 1 calc R U . . .
C20 C 0.06141(10) 0.56562(11) 0.23615(18) 0.0134(3) Uani 1 1 d . . . . .
C21 C 0.14450(12) 0.76322(13) 0.0255(2) 0.0224(4) Uani 1 1 d . . . . .
H21A H 0.1579 0.7319 -0.0636 0.034 Uiso 1 1 calc R U . . .
H21B H 0.1983 0.7780 0.0770 0.034 Uiso 1 1 calc R U . . .
H21C H 0.1129 0.8169 0.0018 0.034 Uiso 1 1 calc R U . . .
C22 C -0.11212(12) 0.72778(15) 0.3474(2) 0.0276(5) Uani 1 1 d . . . . .
H22A H -0.1457 0.7612 0.2759 0.041 Uiso 1 1 calc R U . . .
H22B H -0.0938 0.7665 0.4264 0.041 Uiso 1 1 calc R U . . .
H22C H -0.1478 0.6806 0.3858 0.041 Uiso 1 1 calc R U . . .
C23 C 0.08332(12) 0.47146(12) 0.2635(2) 0.0187(4) Uani 1 1 d . . . . .
H23A H 0.0650 0.4363 0.1800 0.028 Uiso 1 1 calc R U . . .
H23B H 0.0535 0.4512 0.3497 0.028 Uiso 1 1 calc R U . . .
H23C H 0.1458 0.4655 0.2785 0.028 Uiso 1 1 calc R U . . .
B1 B 0.25521(13) 0.52291(14) 0.5475(2) 0.0177(4) Uani 1 1 d . . . . .
F1 F 0.26094(7) 0.56284(8) 0.41365(12) 0.0274(3) Uani 1 1 d . . . . .
F2 F 0.30657(9) 0.56463(11) 0.64686(14) 0.0430(4) Uani 1 1 d . . . . .
F3 F 0.27831(9) 0.43537(9) 0.53591(18) 0.0467(4) Uani 1 1 d . . . . .
F4 F 0.16834(7) 0.52649(8) 0.59134(12) 0.0280(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.316(2) . ?
N1 C6 1.453(2) . ?
N1 C2 1.491(2) . ?
N2 C1 1.319(2) . ?
N2 C15 1.455(2) . ?
N2 C5 1.490(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.521(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.532(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.521(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.397(2) . ?
C6 C11 1.399(2) . ?
C7 C8 1.394(2) . ?
C7 C12 1.512(2) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(3) . ?
C9 C13 1.510(2) . ?
C10 C11 1.394(2) . ?
C10 H10 0.9500 . ?
C11 C14 1.509(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.396(2) . ?
C15 C16 1.398(2) . ?
C16 C17 1.393(2) . ?
C16 C21 1.507(3) . ?
C17 C18 1.390(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(3) . ?
C18 C22 1.513(2) . ?
C19 C20 1.393(2) . ?
C19 H19 0.9500 . ?
C20 C23 1.501(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
B1 F2 1.366(3) . ?
B1 F1 1.386(2) . ?
B1 F3 1.392(3) . ?
B1 F4 1.414(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C6 117.51(14) . . ?
C1 N1 C2 125.65(14) . . ?
C6 N1 C2 116.83(13) . . ?
C1 N2 C15 118.78(14) . . ?
C1 N2 C5 121.50(14) . . ?
C15 N2 C5 118.26(13) . . ?
N1 C1 N2 126.88(16) . . ?
N1 C1 H1 116.6 . . ?
N2 C1 H1 116.6 . . ?
N1 C2 C3 112.11(13) . . ?
N1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C4 113.01(15) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 111.59(14) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
N2 C5 C4 113.84(14) . . ?
N2 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
N2 C5 H5B 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C11 122.53(15) . . ?
C7 C6 N1 118.12(15) . . ?
C11 C6 N1 119.33(15) . . ?
C8 C7 C6 117.47(16) . . ?
C8 C7 C12 119.91(16) . . ?
C6 C7 C12 122.61(15) . . ?
C9 C8 C7 121.94(17) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C10 118.80(16) . . ?
C8 C9 C13 120.90(17) . . ?
C10 C9 C13 120.28(17) . . ?
C11 C10 C9 121.61(16) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C6 117.58(16) . . ?
C10 C11 C14 119.82(15) . . ?
C6 C11 C14 122.60(15) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 122.34(15) . . ?
C20 C15 N2 119.27(15) . . ?
C16 C15 N2 118.36(15) . . ?
C17 C16 C15 117.64(16) . . ?
C17 C16 C21 120.50(16) . . ?
C15 C16 C21 121.86(16) . . ?
C18 C17 C16 121.77(17) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C19 C18 C17 118.76(16) . . ?
C19 C18 C22 120.59(18) . . ?
C17 C18 C22 120.65(18) . . ?
C18 C19 C20 121.80(17) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C19 C20 C15 117.69(16) . . ?
C19 C20 C23 120.04(16) . . ?
C15 C20 C23 122.27(15) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
F2 B1 F1 110.56(17) . . ?
F2 B1 F3 110.73(17) . . ?
F1 B1 F3 109.61(17) . . ?
F2 B1 F4 109.64(16) . . ?
F1 B1 F4 108.34(15) . . ?
F3 B1 F4 107.88(16) . . ?

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
C6 N1 C1 N2 164.85(16) . . . . ?
C2 N1 C1 N2 -14.4(3) . . . . ?
C15 N2 C1 N1 176.13(16) . . . . ?
C5 N2 C1 N1 -17.9(3) . . . . ?
C1 N1 C2 C3 -31.9(2) . . . . ?
C6 N1 C2 C3 148.76(14) . . . . ?
N1 C2 C3 C4 82.32(18) . . . . ?
C2 C3 C4 C5 -39.7(2) . . . . ?
C1 N2 C5 C4 76.4(2) . . . . ?
C15 N2 C5 C4 -117.58(16) . . . . ?
C3 C4 C5 N2 -44.11(19) . . . . ?
C1 N1 C6 C7 -76.6(2) . . . . ?
C2 N1 C6 C7 102.75(18) . . . . ?
C1 N1 C6 C11 104.84(18) . . . . ?
C2 N1 C6 C11 -75.80(19) . . . . ?
C11 C6 C7 C8 -2.7(2) . . . . ?
N1 C6 C7 C8 178.77(14) . . . . ?
C11 C6 C7 C12 177.41(16) . . . . ?
N1 C6 C7 C12 -1.1(2) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C12 C7 C8 C9 -179.62(16) . . . . ?
C7 C8 C9 C10 1.4(3) . . . . ?
C7 C8 C9 C13 -177.05(16) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C13 C9 C10 C11 177.28(16) . . . . ?
C9 C10 C11 C6 -0.9(2) . . . . ?
C9 C10 C11 C14 178.69(16) . . . . ?
C7 C6 C11 C10 2.9(2) . . . . ?
N1 C6 C11 C10 -178.59(14) . . . . ?
C7 C6 C11 C14 -176.67(16) . . . . ?
N1 C6 C11 C14 1.8(2) . . . . ?
C1 N2 C15 C20 -104.26(19) . . . . ?
C5 N2 C15 C20 89.32(19) . . . . ?
C1 N2 C15 C16 77.6(2) . . . . ?
C5 N2 C15 C16 -88.80(19) . . . . ?
C20 C15 C16 C17 -0.5(3) . . . . ?
N2 C15 C16 C17 177.58(15) . . . . ?
C20 C15 C16 C21 178.48(17) . . . . ?
N2 C15 C16 C21 -3.5(2) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C21 C16 C17 C18 -178.88(18) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C16 C17 C18 C22 -179.89(17) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C22 C18 C19 C20 179.90(17) . . . . ?
C18 C19 C20 C15 -0.1(3) . . . . ?
C18 C19 C20 C23 -179.35(17) . . . . ?
C16 C15 C20 C19 0.5(3) . . . . ?
N2 C15 C20 C19 -177.56(15) . . . . ?
C16 C15 C20 C23 179.71(16) . . . . ?
N2 C15 C20 C23 1.7(2) . . . . ?

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_H264
_database_code_depnum_ccdc_archive 'CCDC 1584468'
_audit_update_record             
;
2017-11-08 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 I N2 O0.50'
_chemical_formula_weight         387.25

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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. 
;

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                   17.5096(8)
_cell_length_b                   10.5339(5)
_cell_length_c                   11.1338(6)
_cell_angle_alpha                90
_cell_angle_beta                 126.3150(10)
_cell_angle_gamma                90
_cell_volume                     1654.71(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9887
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      33.43

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_F_000             772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.192
_exptl_absorpt_coefficient_mu    1.932
_shelx_estimated_absorpt_T_min   0.568
_shelx_estimated_absorpt_T_max   0.708
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6848
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Microfocus Source'
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47242
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.664
_diffrn_reflns_theta_max         28.275
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4118
_reflns_number_gt                4083
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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. 
;

_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0137P)²+0.5366P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0130(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1910 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.010(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4118
_refine_ls_number_parameters     190
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0113
_refine_ls_R_factor_gt           0.0111
_refine_ls_wR_factor_ref         0.0274
_refine_ls_wR_factor_gt          0.0274
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
I1 I 0.43973(2) 0.07770(2) 0.70244(2) 0.01770(5) Uani 1 1 d . . . . .
N1 N 0.31696(11) 0.42374(14) 0.39164(16) 0.0119(3) Uani 1 1 d . . . . .
N2 N 0.24521(11) 0.39935(15) 0.13608(16) 0.0124(3) Uani 1 1 d . . . . .
C1 C 0.31728(13) 0.43047(17) 0.2731(2) 0.0128(3) Uani 1 1 d . . . . .
H1 H 0.3735 0.4599 0.2877 0.015 Uiso 1 1 calc R U . . .
C2 C 0.25878(13) 0.33383(17) 0.40975(19) 0.0142(3) Uani 1 1 d . . . . .
H2A H 0.2032 0.3795 0.3906 0.017 Uiso 1 1 calc R U . . .
H2B H 0.2969 0.3031 0.5140 0.017 Uiso 1 1 calc R U . . .
C3 C 0.22448(14) 0.21992(18) 0.3050(2) 0.0178(4) Uani 1 1 d . . . . .
H3A H 0.2063 0.1511 0.3441 0.021 Uiso 1 1 calc R U . . .
H3B H 0.2775 0.1884 0.3044 0.021 Uiso 1 1 calc R U . . .
C4 C 0.14008(14) 0.2495(2) 0.1446(2) 0.0224(4) Uani 1 1 d . . . . .
H4A H 0.1365 0.1852 0.0766 0.027 Uiso 1 1 calc R U . . .
H4B H 0.0807 0.2451 0.1365 0.027 Uiso 1 1 calc R U . . .
C5 C 0.14967(14) 0.3810(2) 0.0982(2) 0.0161(4) Uani 1 1 d . . . . .
H5A H 0.1016 0.3916 -0.0106 0.019 Uiso 1 1 calc R U . . .
H5B H 0.1378 0.4462 0.1493 0.019 Uiso 1 1 calc R U . . .
C6 C 0.38200(16) 0.5066(2) 0.5134(2) 0.0132(4) Uani 1 1 d . . . . .
C7 C 0.38598(18) 0.6327(2) 0.4804(3) 0.0182(5) Uani 1 1 d . . . . .
H7 H 0.3451 0.6619 0.3804 0.022 Uiso 1 1 calc R U . . .
C8 C 0.44916(16) 0.71586(19) 0.5926(2) 0.0224(4) Uani 1 1 d . . . . .
H8 H 0.4526 0.8017 0.5699 0.027 Uiso 1 1 calc R U . . .
C9 C 0.50739(15) 0.6730(2) 0.7383(2) 0.0209(4) Uani 1 1 d . . . . .
H9 H 0.5513 0.7294 0.8157 0.025 Uiso 1 1 calc R U . . .
C10 C 0.50204(14) 0.54801(17) 0.7719(2) 0.0167(4) Uani 1 1 d . . . . .
H10 H 0.5414 0.5201 0.8725 0.020 Uiso 1 1 calc R U . . .
C11 C 0.43969(13) 0.46323(17) 0.6599(2) 0.0145(3) Uani 1 1 d . . . . .
H11 H 0.4365 0.3774 0.6828 0.017 Uiso 1 1 calc R U . . .
C12 C 0.26210(13) 0.37710(17) 0.02592(19) 0.0126(3) Uani 1 1 d . . . . .
C13 C 0.33617(13) 0.29769(18) 0.0612(2) 0.0160(3) Uani 1 1 d . . . . .
H13 H 0.3742 0.2576 0.1560 0.019 Uiso 1 1 calc R U . . .
C14 C 0.35411(16) 0.2773(2) -0.0436(3) 0.0216(4) Uani 1 1 d . . . . .
H14 H 0.4049 0.2239 -0.0204 0.026 Uiso 1 1 calc R U . . .
C15 C 0.29733(16) 0.3356(2) -0.1821(2) 0.0235(4) Uani 1 1 d . . . . .
H15 H 0.3098 0.3222 -0.2534 0.028 Uiso 1 1 calc R U . . .
C16 C 0.22245(15) 0.4132(2) -0.2176(2) 0.0215(4) Uani 1 1 d . . . . .
H16 H 0.1837 0.4518 -0.3131 0.026 Uiso 1 1 calc R U . . .
C17 C 0.20387(14) 0.43483(18) -0.1134(2) 0.0167(3) Uani 1 1 d . . . . .
H17 H 0.1527 0.4877 -0.1370 0.020 Uiso 1 1 calc R U . . .
O1W O 0.5000 0.2592(2) 0.5000 0.0334(5) Uani 1 2 d DS T P . .
H1W H 0.517(2) 0.211(2) 0.461(3) 0.040 Uiso 1 1 d D 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
N1 C1 1.325(2) . ?
N1 C6 1.438(3) . ?
N1 C2 1.489(2) . ?
N2 C1 1.322(2) . ?
N2 C12 1.441(2) . ?
N2 C5 1.476(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.527(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.531(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.522(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.391(3) . ?
C6 C11 1.392(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.390(3) . ?
C12 C17 1.394(2) . ?
C13 C14 1.392(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.396(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O1W H1W 0.831(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C6 115.99(16) . . ?
C1 N1 C2 125.13(15) . . ?
C6 N1 C2 118.80(14) . . ?
C1 N2 C12 119.06(15) . . ?
C1 N2 C5 120.57(15) . . ?
C12 N2 C5 120.30(15) . . ?
N2 C1 N1 124.89(16) . . ?
N2 C1 H1 117.6 . . ?
N1 C1 H1 117.6 . . ?
N1 C2 C3 112.79(14) . . ?
N1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 113.72(17) . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 110.91(16) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.0 . . ?
N2 C5 C4 110.87(16) . . ?
N2 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C11 120.5(2) . . ?
C7 C6 N1 117.8(2) . . ?
C11 C6 N1 121.68(18) . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.4(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C10 120.37(19) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 120.69(18) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C6 118.66(17) . . ?
C10 C11 H11 120.7 . . ?
C6 C11 H11 120.7 . . ?
C13 C12 C17 121.47(16) . . ?
C13 C12 N2 119.00(16) . . ?
C17 C12 N2 119.53(16) . . ?
C12 C13 C14 119.45(19) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.65(18) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 120.33(19) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 118.47(18) . . ?
C12 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?

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
C12 N2 C1 N1 -162.91(17) . . . . ?
C5 N2 C1 N1 13.9(3) . . . . ?
C6 N1 C1 N2 -155.27(18) . . . . ?
C2 N1 C1 N2 27.9(3) . . . . ?
C1 N1 C2 C3 19.6(2) . . . . ?
C6 N1 C2 C3 -157.09(16) . . . . ?
N1 C2 C3 C4 -77.8(2) . . . . ?
C2 C3 C4 C5 38.2(2) . . . . ?
C1 N2 C5 C4 -81.0(2) . . . . ?
C12 N2 C5 C4 95.76(19) . . . . ?
C3 C4 C5 N2 48.2(2) . . . . ?
C1 N1 C6 C7 46.4(3) . . . . ?
C2 N1 C6 C7 -136.62(19) . . . . ?
C1 N1 C6 C11 -133.48(19) . . . . ?
C2 N1 C6 C11 43.6(3) . . . . ?
C11 C6 C7 C8 1.7(3) . . . . ?
N1 C6 C7 C8 -178.2(2) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C11 1.3(3) . . . . ?
C9 C10 C11 C6 -0.7(3) . . . . ?
C7 C6 C11 C10 -0.8(3) . . . . ?
N1 C6 C11 C10 178.98(18) . . . . ?
C1 N2 C12 C13 48.6(2) . . . . ?
C5 N2 C12 C13 -128.24(19) . . . . ?
C1 N2 C12 C17 -131.71(18) . . . . ?
C5 N2 C12 C17 51.5(2) . . . . ?
C17 C12 C13 C14 1.4(3) . . . . ?
N2 C12 C13 C14 -178.89(17) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C13 C12 C17 C16 -1.2(3) . . . . ?
N2 C12 C17 C16 179.13(17) . . . . ?
C15 C16 C17 C12 0.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1W I1 0.831(12) 2.734(12) 3.5590(13) 172(2) 2_656

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.056

