# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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data_b14078

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H27 N4 O3'
_chemical_formula_weight         359.44

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'

_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                   18.930(7)
_cell_length_b                   5.8718(19)
_cell_length_c                   18.364(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.364(12)
_cell_angle_gamma                90
_cell_volume                     1968.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    7662
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      33.03

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6509
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50062
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.116
_diffrn_reflns_theta_max         37.015
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8901
_reflns_number_gt                5922
_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       Apex2
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    XS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    XP
_computing_publication_material  cif2tables.py

_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)+(0.0809P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8901
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1527
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
O2 O 0.52093(4) 0.13374(14) 0.36449(4) 0.02513(18) Uani 1 1 d . . . . .
O3 O 0.53001(4) 0.23532(13) 0.48544(4) 0.02426(17) Uani 1 1 d . . . . .
O1 O 0.02312(4) 0.56115(11) 0.13462(4) 0.01799(15) Uani 1 1 d . . . . .
N1 N 0.12501(4) 0.58480(13) 0.23500(5) 0.01432(15) Uani 1 1 d . . . . .
N2 N 0.19593(4) 0.52956(13) 0.26993(5) 0.01546(16) Uani 1 1 d . . . . .
N3 N 0.12668(4) 0.36515(13) 0.13112(4) 0.01376(15) Uani 1 1 d . . . . .
N4 N 0.19790(4) 0.30348(13) 0.16285(4) 0.01417(15) Uani 1 1 d . . . . .
C5 C 0.12716(6) 0.96646(17) 0.28948(7) 0.0221(2) Uani 1 1 d . . . . .
H1 H 0.1785(8) 0.954(2) 0.3161(8) 0.033(4) Uiso 1 1 d . . . . .
H16 H 0.1025(7) 1.063(2) 0.3198(8) 0.031(4) Uiso 1 1 d . . . . .
H17 H 0.1251(7) 1.032(3) 0.2386(9) 0.038(4) Uiso 1 1 d . . . . .
C3 C 0.08959(5) 0.73605(15) 0.27913(5) 0.01513(17) Uani 1 1 d . . . . .
H15 H 0.0394(6) 0.749(2) 0.2479(7) 0.018(3) Uiso 1 1 d . . . . .
C1 C 0.22795(5) 0.39023(15) 0.23102(5) 0.01327(16) Uani 1 1 d . . . . .
C9 C 0.30460(5) 0.32419(15) 0.26777(5) 0.01392(17) Uani 1 1 d . . . . .
C14 C 0.34950(5) 0.46613(16) 0.32131(6) 0.01763(19) Uani 1 1 d . . . . .
H7 H 0.3329(7) 0.607(2) 0.3324(8) 0.030(3) Uiso 1 1 d . . . . .
C13 C 0.42176(5) 0.40828(17) 0.35595(6) 0.0207(2) Uani 1 1 d . . . . .
H23 H 0.4532(7) 0.507(2) 0.3910(8) 0.030(4) Uiso 1 1 d . . . . .
C12 C 0.44829(5) 0.20342(17) 0.33630(6) 0.01890(19) Uani 1 1 d . . . . .
C15 C 0.55671(5) 0.15205(16) 0.43948(6) 0.01729(18) Uani 1 1 d . . . . .
C16 C 0.63284(5) 0.04871(16) 0.45386(6) 0.01743(19) Uani 1 1 d . . . . .
C17 C 0.62431(6) -0.20878(19) 0.43995(8) 0.0265(2) Uani 1 1 d . . . . .
H2 H 0.5962(8) -0.282(3) 0.4697(9) 0.042(4) Uiso 1 1 d . . . . .
H5 H 0.6735(8) -0.275(2) 0.4486(8) 0.033(4) Uiso 1 1 d . . . . .
H6 H 0.5977(8) -0.241(3) 0.3852(9) 0.039(4) Uiso 1 1 d . . . . .
C18 C 0.67268(6) 0.15571(19) 0.39966(7) 0.0233(2) Uani 1 1 d . . . . .
H3 H 0.6764(8) 0.320(3) 0.4049(8) 0.038(4) Uiso 1 1 d . . . . .
H4 H 0.6477(7) 0.124(2) 0.3452(9) 0.033(4) Uiso 1 1 d . . . . .
H27 H 0.7234(7) 0.092(2) 0.4079(7) 0.027(3) Uiso 1 1 d . . . . .
C2 C 0.08670(5) 0.50793(14) 0.16465(5) 0.01322(17) Uani 1 1 d . . . . .
C6 C 0.09437(5) 0.27098(16) 0.05490(5) 0.01506(17) Uani 1 1 d . . . . .
H14 H 0.0437(7) 0.332(2) 0.0392(7) 0.021(3) Uiso 1 1 d . . . . .
C8 C 0.09363(6) 0.01228(17) 0.05905(7) 0.0229(2) Uani 1 1 d . . . . .
H8 H 0.0644(8) -0.037(2) 0.0899(8) 0.034(4) Uiso 1 1 d . . . . .
H9 H 0.1459(7) -0.043(2) 0.0782(8) 0.026(3) Uiso 1 1 d . . . . .
H10 H 0.0745(7) -0.048(2) 0.0105(8) 0.026(3) Uiso 1 1 d . . . . .
C7 C 0.13617(6) 0.35759(19) 0.00079(6) 0.0217(2) Uani 1 1 d . . . . .
H11 H 0.1868(7) 0.289(2) 0.0144(7) 0.027(3) Uiso 1 1 d . . . . .
H12 H 0.1403(8) 0.528(2) 0.0048(8) 0.037(4) Uiso 1 1 d . . . . .
H13 H 0.1122(7) 0.308(2) -0.0492(8) 0.030(4) Uiso 1 1 d . . . . .
C4 C 0.08997(6) 0.62444(18) 0.35368(6) 0.0217(2) Uani 1 1 d . . . . .
H18 H 0.0640(8) 0.482(3) 0.3457(8) 0.040(4) Uiso 1 1 d . . . . .
H19 H 0.0672(7) 0.724(2) 0.3862(8) 0.032(4) Uiso 1 1 d . . . . .
H20 H 0.1401(6) 0.598(2) 0.3852(7) 0.018(3) Uiso 1 1 d . . . . .
C10 C 0.33291(5) 0.11999(17) 0.24869(6) 0.01844(19) Uani 1 1 d . . . . .
H21 H 0.3028(7) 0.022(2) 0.2103(8) 0.025(3) Uiso 1 1 d . . . . .
C11 C 0.40481(6) 0.05928(17) 0.28323(6) 0.0204(2) Uani 1 1 d . . . . .
H22 H 0.4256(7) -0.083(2) 0.2685(8) 0.030(4) Uiso 1 1 d . . . . .
C19 C 0.67474(6) 0.0954(2) 0.53556(7) 0.0264(2) Uani 1 1 d . . . . .
H24 H 0.6808(8) 0.264(2) 0.5420(8) 0.035(4) Uiso 1 1 d . . . . .
H25 H 0.7226(8) 0.022(2) 0.5438(8) 0.038(4) Uiso 1 1 d . . . . .
H26 H 0.6484(8) 0.030(3) 0.5724(9) 0.042(4) Uiso 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
O2 C15 1.3684(13) . ?
O2 C12 1.3962(12) . ?
O3 C15 1.1970(12) . ?
O1 C2 1.2242(12) . ?
N1 N2 1.3649(11) . ?
N1 C2 1.3792(13) . ?
N1 C3 1.4775(12) . ?
N2 C1 1.3330(12) . ?
N3 N4 1.3684(11) . ?
N3 C2 1.3789(12) . ?
N3 C6 1.4783(12) . ?
N4 C1 1.3315(12) . ?
C5 C3 1.5169(14) . ?
C5 H1 0.967(14) . ?
C5 H16 0.992(14) . ?
C5 H17 1.002(16) . ?
C3 C4 1.5160(14) . ?
C3 H15 0.974(12) . ?
C1 C9 1.4806(13) . ?
C9 C14 1.3933(13) . ?
C9 C10 1.3955(13) . ?
C14 C13 1.3893(14) . ?
C14 H7 0.926(14) . ?
C13 C12 1.3875(14) . ?
C13 H23 0.951(14) . ?
C12 C11 1.3851(15) . ?
C15 C16 1.5209(14) . ?
C16 C19 1.5247(15) . ?
C16 C18 1.5337(15) . ?
C16 C17 1.5348(15) . ?
C17 H2 0.957(15) . ?
C17 H5 0.982(14) . ?
C17 H6 1.016(15) . ?
C18 H3 0.968(15) . ?
C18 H4 1.004(15) . ?
C18 H27 1.004(13) . ?
C6 C7 1.5128(14) . ?
C6 C8 1.5212(14) . ?
C6 H14 0.993(12) . ?
C8 H8 0.936(15) . ?
C8 H9 1.012(13) . ?
C8 H10 0.938(14) . ?
C7 H11 1.007(13) . ?
C7 H12 1.004(14) . ?
C7 H13 0.957(13) . ?
C4 H18 0.961(15) . ?
C4 H19 1.009(14) . ?
C4 H20 0.984(12) . ?
C10 C11 1.3872(14) . ?
C10 H21 0.968(13) . ?
C11 H22 0.993(14) . ?
C19 H24 0.999(14) . ?
C19 H25 0.978(14) . ?
C19 H26 1.015(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
C15 O2 C12 121.76(8) . . ?
N2 N1 C2 124.75(8) . . ?
N2 N1 C3 114.70(8) . . ?
C2 N1 C3 120.54(8) . . ?
C1 N2 N1 115.11(8) . . ?
N4 N3 C2 124.49(8) . . ?
N4 N3 C6 114.70(7) . . ?
C2 N3 C6 120.79(8) . . ?
C1 N4 N3 115.24(7) . . ?
C3 C5 H1 111.9(8) . . ?
C3 C5 H16 107.7(8) . . ?
H1 C5 H16 108.4(11) . . ?
C3 C5 H17 108.9(8) . . ?
H1 C5 H17 106.6(12) . . ?
H16 C5 H17 113.5(11) . . ?
N1 C3 C4 109.95(8) . . ?
N1 C3 C5 109.81(8) . . ?
C4 C3 C5 112.49(9) . . ?
N1 C3 H15 103.8(7) . . ?
C4 C3 H15 109.6(7) . . ?
C5 C3 H15 110.9(7) . . ?
N4 C1 N2 126.67(8) . . ?
N4 C1 C9 116.83(8) . . ?
N2 C1 C9 116.50(8) . . ?
C14 C9 C10 119.21(9) . . ?
C14 C9 C1 120.40(8) . . ?
C10 C9 C1 120.39(8) . . ?
C13 C14 C9 121.30(9) . . ?
C13 C14 H7 117.9(8) . . ?
C9 C14 H7 120.7(8) . . ?
C12 C13 C14 118.24(9) . . ?
C12 C13 H23 120.1(8) . . ?
C14 C13 H23 121.7(8) . . ?
C11 C12 C13 121.62(9) . . ?
C11 C12 O2 115.15(9) . . ?
C13 C12 O2 123.12(9) . . ?
O3 C15 O2 123.56(9) . . ?
O3 C15 C16 126.74(9) . . ?
O2 C15 C16 109.69(8) . . ?
C15 C16 C19 108.73(8) . . ?
C15 C16 C18 109.28(8) . . ?
C19 C16 C18 110.36(9) . . ?
C15 C16 C17 108.13(8) . . ?
C19 C16 C17 110.20(9) . . ?
C18 C16 C17 110.10(9) . . ?
C16 C17 H2 113.3(9) . . ?
C16 C17 H5 108.0(8) . . ?
H2 C17 H5 112.1(12) . . ?
C16 C17 H6 110.7(8) . . ?
H2 C17 H6 105.9(12) . . ?
H5 C17 H6 106.7(12) . . ?
C16 C18 H3 112.2(9) . . ?
C16 C18 H4 112.7(8) . . ?
H3 C18 H4 106.7(12) . . ?
C16 C18 H27 111.4(8) . . ?
H3 C18 H27 108.3(11) . . ?
H4 C18 H27 105.1(11) . . ?
O1 C2 N3 122.99(9) . . ?
O1 C2 N1 123.27(8) . . ?
N3 C2 N1 113.75(8) . . ?
N3 C6 C7 109.82(8) . . ?
N3 C6 C8 109.45(8) . . ?
C7 C6 C8 112.46(9) . . ?
N3 C6 H14 105.4(7) . . ?
C7 C6 H14 108.8(7) . . ?
C8 C6 H14 110.7(7) . . ?
C6 C8 H8 110.6(9) . . ?
C6 C8 H9 108.4(7) . . ?
H8 C8 H9 111.8(12) . . ?
C6 C8 H10 109.6(8) . . ?
H8 C8 H10 108.6(12) . . ?
H9 C8 H10 107.9(11) . . ?
C6 C7 H11 109.4(7) . . ?
C6 C7 H12 109.4(8) . . ?
H11 C7 H12 109.1(11) . . ?
C6 C7 H13 109.3(8) . . ?
H11 C7 H13 107.1(11) . . ?
H12 C7 H13 112.5(12) . . ?
C3 C4 H18 111.0(9) . . ?
C3 C4 H19 112.5(8) . . ?
H18 C4 H19 108.2(11) . . ?
C3 C4 H20 111.9(7) . . ?
H18 C4 H20 109.1(11) . . ?
H19 C4 H20 103.8(10) . . ?
C11 C10 C9 120.11(9) . . ?
C11 C10 H21 119.9(7) . . ?
C9 C10 H21 120.0(7) . . ?
C12 C11 C10 119.52(9) . . ?
C12 C11 H22 120.2(8) . . ?
C10 C11 H22 120.3(8) . . ?
C16 C19 H24 108.0(8) . . ?
C16 C19 H25 107.0(8) . . ?
H24 C19 H25 110.1(11) . . ?
C16 C19 H26 111.7(9) . . ?
H24 C19 H26 110.7(12) . . ?
H25 C19 H26 109.3(12) . . ?

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
C2 N1 N2 C1 -0.23(13) . . . . ?
C3 N1 N2 C1 178.98(8) . . . . ?
C2 N3 N4 C1 0.59(12) . . . . ?
C6 N3 N4 C1 178.98(8) . . . . ?
N2 N1 C3 C4 -59.11(11) . . . . ?
C2 N1 C3 C4 120.15(9) . . . . ?
N2 N1 C3 C5 65.18(11) . . . . ?
C2 N1 C3 C5 -115.57(10) . . . . ?
N3 N4 C1 N2 -0.54(13) . . . . ?
N3 N4 C1 C9 178.98(7) . . . . ?
N1 N2 C1 N4 0.37(14) . . . . ?
N1 N2 C1 C9 -179.14(8) . . . . ?
N4 C1 C9 C14 154.17(9) . . . . ?
N2 C1 C9 C14 -26.27(13) . . . . ?
N4 C1 C9 C10 -25.24(13) . . . . ?
N2 C1 C9 C10 154.32(9) . . . . ?
C10 C9 C14 C13 0.01(15) . . . . ?
C1 C9 C14 C13 -179.41(9) . . . . ?
C9 C14 C13 C12 -0.49(16) . . . . ?
C14 C13 C12 C11 0.52(17) . . . . ?
C14 C13 C12 O2 176.53(10) . . . . ?
C15 O2 C12 C11 -138.43(10) . . . . ?
C15 O2 C12 C13 45.32(15) . . . . ?
C12 O2 C15 O3 -2.83(15) . . . . ?
C12 O2 C15 C16 176.28(9) . . . . ?
O3 C15 C16 C19 -7.40(15) . . . . ?
O2 C15 C16 C19 173.52(9) . . . . ?
O3 C15 C16 C18 -127.92(11) . . . . ?
O2 C15 C16 C18 53.01(11) . . . . ?
O3 C15 C16 C17 112.24(12) . . . . ?
O2 C15 C16 C17 -66.83(11) . . . . ?
N4 N3 C2 O1 179.54(8) . . . . ?
C6 N3 C2 O1 1.25(13) . . . . ?
N4 N3 C2 N1 -0.47(12) . . . . ?
C6 N3 C2 N1 -178.77(8) . . . . ?
N2 N1 C2 O1 -179.73(8) . . . . ?
C3 N1 C2 O1 1.09(13) . . . . ?
N2 N1 C2 N3 0.29(12) . . . . ?
C3 N1 C2 N3 -178.89(8) . . . . ?
N4 N3 C6 C7 -62.02(10) . . . . ?
C2 N3 C6 C7 116.43(10) . . . . ?
N4 N3 C6 C8 61.89(10) . . . . ?
C2 N3 C6 C8 -119.66(9) . . . . ?
C14 C9 C10 C11 0.46(15) . . . . ?
C1 C9 C10 C11 179.88(9) . . . . ?
C13 C12 C11 C10 -0.07(17) . . . . ?
O2 C12 C11 C10 -176.37(9) . . . . ?
C9 C10 C11 C12 -0.44(16) . . . . ?

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.076

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 991914'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_n14031

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H19 N4 O'
_chemical_formula_weight         259.33

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   16.219(7)
_cell_length_b                   15.484(9)
_cell_length_c                   5.7192(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1436.4(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5495
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.34

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6702
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12489
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.638
_diffrn_reflns_theta_max         27.099
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2645
_reflns_number_gt                2339
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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       Apex2
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    Sir2011
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    XP
_computing_publication_material  cif2tables.py

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.1951P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2645
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0767
_refine_ls_wR_factor_gt          0.0735
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
O1 O 0.58824(7) 0.57824(7) 0.6557(3) 0.0290(3) Uani 1 1 d . . . . .
N1 N 0.58412(8) 0.71384(9) 0.8152(3) 0.0246(3) Uani 1 1 d . . . . .
N4 N 0.43190(8) 0.73772(9) 0.6285(3) 0.0272(4) Uani 1 1 d . . . . .
N2 N 0.54422(9) 0.79052(9) 0.8553(3) 0.0270(4) Uani 1 1 d . . . . .
N3 N 0.47607(8) 0.66400(9) 0.5890(3) 0.0249(4) Uani 1 1 d . . . . .
C2 C 0.55185(10) 0.64676(10) 0.6849(3) 0.0233(4) Uani 1 1 d . . . . .
C9 C 0.42397(10) 0.87864(11) 0.7973(4) 0.0273(4) Uani 1 1 d . . . . .
C1 C 0.46997(11) 0.79689(11) 0.7593(3) 0.0250(4) Uani 1 1 d . . . . .
C3 C 0.66680(10) 0.70630(11) 0.9217(4) 0.0270(4) Uani 1 1 d . . . . .
H4A H 0.6919 0.6507 0.8682 0.032 Uiso 1 1 calc R U . . .
C6 C 0.43250(11) 0.59650(11) 0.4527(3) 0.0263(4) Uani 1 1 d . . . . .
H6A H 0.4744 0.5540 0.3962 0.032 Uiso 1 1 calc R U . . .
C5 C 0.72131(11) 0.77963(12) 0.8381(4) 0.0337(5) Uani 1 1 d . . . . .
H7A H 0.7245 0.7786 0.6670 0.050 Uiso 1 1 calc R U . . .
H7B H 0.7767 0.7728 0.9039 0.050 Uiso 1 1 calc R U . . .
H7C H 0.6979 0.8348 0.8894 0.050 Uiso 1 1 calc R U . . .
C10 C 0.36170(11) 0.90265(12) 0.6424(5) 0.0344(5) Uani 1 1 d . . . . .
H8A H 0.3485 0.8663 0.5138 0.041 Uiso 1 1 calc R U . . .
C14 C 0.44249(12) 0.93215(13) 0.9857(4) 0.0355(5) Uani 1 1 d . . . . .
H9A H 0.4846 0.9162 1.0926 0.043 Uiso 1 1 calc R U . . .
C13 C 0.39935(12) 1.00894(13) 1.0176(5) 0.0406(5) Uani 1 1 d . . . . .
H10A H 0.4122 1.0455 1.1459 0.049 Uiso 1 1 calc R U . . .
C12 C 0.33791(12) 1.03201(12) 0.8627(5) 0.0409(6) Uani 1 1 d . . . . .
H12A H 0.3085 1.0844 0.8851 0.049 Uiso 1 1 calc R U . . .
C4 C 0.65893(14) 0.70311(14) 1.1862(4) 0.0406(5) Uani 1 1 d . . . . .
H13A H 0.6237 0.6544 1.2308 0.061 Uiso 1 1 calc R U . . .
H13B H 0.6343 0.7570 1.2424 0.061 Uiso 1 1 calc R U . . .
H13C H 0.7137 0.6959 1.2560 0.061 Uiso 1 1 calc R U . . .
C11 C 0.31881(12) 0.97933(12) 0.6750(5) 0.0403(5) Uani 1 1 d . . . . .
H14A H 0.2765 0.9955 0.5688 0.048 Uiso 1 1 calc R U . . .
C8 C 0.37215(11) 0.54902(12) 0.6107(4) 0.0298(4) Uani 1 1 d . . . . .
H31A H 0.4019 0.5247 0.7446 0.045 Uiso 1 1 calc R U . . .
H31B H 0.3457 0.5023 0.5226 0.045 Uiso 1 1 calc R U . . .
H31C H 0.3300 0.5894 0.6665 0.045 Uiso 1 1 calc R U . . .
C7 C 0.39093(14) 0.63610(13) 0.2413(4) 0.0392(5) Uani 1 1 d . . . . .
H32A H 0.4322 0.6658 0.1453 0.059 Uiso 1 1 calc R U . . .
H32B H 0.3491 0.6776 0.2929 0.059 Uiso 1 1 calc R U . . .
H32C H 0.3646 0.5905 0.1489 0.059 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
O1 C2 1.226(2) . ?
N1 N2 1.3714(19) . ?
N1 C2 1.381(2) . ?
N1 C3 1.478(2) . ?
N4 C1 1.334(2) . ?
N4 N3 1.366(2) . ?
N2 C1 1.327(2) . ?
N3 C2 1.372(2) . ?
N3 C6 1.483(2) . ?
C9 C14 1.392(3) . ?
C9 C10 1.394(3) . ?
C9 C1 1.485(2) . ?
C3 C5 1.516(3) . ?
C3 C4 1.519(3) . ?
C3 H4A 1.0000 . ?
C6 C7 1.514(3) . ?
C6 C8 1.521(3) . ?
C6 H6A 1.0000 . ?
C5 H7A 0.9800 . ?
C5 H7B 0.9800 . ?
C5 H7C 0.9800 . ?
C10 C11 1.389(3) . ?
C10 H8A 0.9500 . ?
C14 C13 1.392(3) . ?
C14 H9A 0.9500 . ?
C13 C12 1.380(3) . ?
C13 H10A 0.9500 . ?
C12 C11 1.383(3) . ?
C12 H12A 0.9500 . ?
C4 H13A 0.9800 . ?
C4 H13B 0.9800 . ?
C4 H13C 0.9800 . ?
C11 H14A 0.9500 . ?
C8 H31A 0.9800 . ?
C8 H31B 0.9800 . ?
C8 H31C 0.9800 . ?
C7 H32A 0.9800 . ?
C7 H32B 0.9800 . ?
C7 H32C 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
N2 N1 C2 124.23(14) . . ?
N2 N1 C3 115.32(14) . . ?
C2 N1 C3 120.45(14) . . ?
C1 N4 N3 115.06(14) . . ?
C1 N2 N1 115.05(14) . . ?
N4 N3 C2 124.48(14) . . ?
N4 N3 C6 115.20(14) . . ?
C2 N3 C6 119.98(14) . . ?
O1 C2 N3 123.05(16) . . ?
O1 C2 N1 122.83(16) . . ?
N3 C2 N1 114.12(14) . . ?
C14 C9 C10 119.30(17) . . ?
C14 C9 C1 120.79(18) . . ?
C10 C9 C1 119.91(18) . . ?
N2 C1 N4 126.92(16) . . ?
N2 C1 C9 117.31(16) . . ?
N4 C1 C9 115.76(16) . . ?
N1 C3 C5 109.87(15) . . ?
N1 C3 C4 109.69(16) . . ?
C5 C3 C4 112.80(17) . . ?
N1 C3 H4A 108.1 . . ?
C5 C3 H4A 108.1 . . ?
C4 C3 H4A 108.1 . . ?
N3 C6 C7 110.27(15) . . ?
N3 C6 C8 109.58(15) . . ?
C7 C6 C8 112.53(16) . . ?
N3 C6 H6A 108.1 . . ?
C7 C6 H6A 108.1 . . ?
C8 C6 H6A 108.1 . . ?
C3 C5 H7A 109.5 . . ?
C3 C5 H7B 109.5 . . ?
H7A C5 H7B 109.5 . . ?
C3 C5 H7C 109.5 . . ?
H7A C5 H7C 109.5 . . ?
H7B C5 H7C 109.5 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H8A 119.8 . . ?
C9 C10 H8A 119.8 . . ?
C13 C14 C9 120.1(2) . . ?
C13 C14 H9A 119.9 . . ?
C9 C14 H9A 119.9 . . ?
C12 C13 C14 120.0(2) . . ?
C12 C13 H10A 120.0 . . ?
C14 C13 H10A 120.0 . . ?
C13 C12 C11 120.47(18) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C3 C4 H13A 109.5 . . ?
C3 C4 H13B 109.5 . . ?
H13A C4 H13B 109.5 . . ?
C3 C4 H13C 109.5 . . ?
H13A C4 H13C 109.5 . . ?
H13B C4 H13C 109.5 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H14A 120.1 . . ?
C10 C11 H14A 120.1 . . ?
C6 C8 H31A 109.5 . . ?
C6 C8 H31B 109.5 . . ?
H31A C8 H31B 109.5 . . ?
C6 C8 H31C 109.5 . . ?
H31A C8 H31C 109.5 . . ?
H31B C8 H31C 109.5 . . ?
C6 C7 H32A 109.5 . . ?
C6 C7 H32B 109.5 . . ?
H32A C7 H32B 109.5 . . ?
C6 C7 H32C 109.5 . . ?
H32A C7 H32C 109.5 . . ?
H32B C7 H32C 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
C2 N1 N2 C1 0.3(3) . . . . ?
C3 N1 N2 C1 -179.95(16) . . . . ?
C1 N4 N3 C2 4.0(3) . . . . ?
C1 N4 N3 C6 177.35(15) . . . . ?
N4 N3 C2 O1 176.26(17) . . . . ?
C6 N3 C2 O1 3.2(3) . . . . ?
N4 N3 C2 N1 -4.5(2) . . . . ?
C6 N3 C2 N1 -177.52(15) . . . . ?
N2 N1 C2 O1 -178.54(17) . . . . ?
C3 N1 C2 O1 1.7(3) . . . . ?
N2 N1 C2 N3 2.2(3) . . . . ?
C3 N1 C2 N3 -177.55(15) . . . . ?
N1 N2 C1 N4 -0.9(3) . . . . ?
N1 N2 C1 C9 -179.99(16) . . . . ?
N3 N4 C1 N2 -1.1(3) . . . . ?
N3 N4 C1 C9 178.00(16) . . . . ?
C14 C9 C1 N2 -22.2(3) . . . . ?
C10 C9 C1 N2 157.47(18) . . . . ?
C14 C9 C1 N4 158.55(18) . . . . ?
C10 C9 C1 N4 -21.7(3) . . . . ?
N2 N1 C3 C5 -56.8(2) . . . . ?
C2 N1 C3 C5 123.01(18) . . . . ?
N2 N1 C3 C4 67.8(2) . . . . ?
C2 N1 C3 C4 -112.46(19) . . . . ?
N4 N3 C6 C7 46.2(2) . . . . ?
C2 N3 C6 C7 -140.14(17) . . . . ?
N4 N3 C6 C8 -78.19(19) . . . . ?
C2 N3 C6 C8 95.46(19) . . . . ?
C14 C9 C10 C11 0.3(3) . . . . ?
C1 C9 C10 C11 -179.41(18) . . . . ?
C10 C9 C14 C13 -0.3(3) . . . . ?
C1 C9 C14 C13 179.40(18) . . . . ?
C9 C14 C13 C12 0.2(3) . . . . ?
C14 C13 C12 C11 -0.1(3) . . . . ?
C13 C12 C11 C10 0.1(3) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?

_refine_diff_density_max         0.141
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 991915'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_n14024

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H19 B F4 N4 O'
_chemical_formula_weight         346.14

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'
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'

_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                   8.1059(16)
_cell_length_b                   13.501(5)
_cell_length_c                   15.435(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.864(10)
_cell_angle_gamma                90
_cell_volume                     1664.3(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9924
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      30.57

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6809
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57902
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.018
_diffrn_reflns_theta_max         32.078
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5606
_reflns_number_gt                4140
_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       Apex2
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    XS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    XP
_computing_publication_material  cif2tables.py

_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)+(0.0750P)²+1.0171P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5606
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1685
_refine_ls_wR_factor_gt          0.1489
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
N3 N 0.63184(14) 0.18935(9) 0.73811(8) 0.0219(2) Uani 1 1 d . . . . .
O1 O 0.62303(16) 0.19498(10) 0.58801(8) 0.0381(3) Uani 1 1 d . . . . .
F1 F 0.12954(16) 0.40151(12) 0.73106(11) 0.0714(4) Uani 1 1 d . . . . .
N1 N 0.39479(15) 0.13566(9) 0.64325(7) 0.0238(2) Uani 1 1 d . . . . .
C9 C 0.35316(17) 0.07752(10) 0.86700(8) 0.0223(3) Uani 1 1 d . . . . .
F2 F 0.36377(18) 0.47812(9) 0.79869(10) 0.0597(4) Uani 1 1 d . . . . .
N2 N 0.32874(15) 0.10440(9) 0.70981(7) 0.0237(2) Uani 1 1 d . . . . .
F3 F 0.38031(18) 0.33485(9) 0.72516(7) 0.0544(4) Uani 1 1 d . . . . .
C2 C 0.55646(19) 0.17431(11) 0.64952(9) 0.0255(3) Uani 1 1 d . . . . .
N4 N 0.57045(15) 0.15924(9) 0.80537(7) 0.0222(2) Uani 1 1 d . . . . .
F4 F 0.2830(2) 0.33287(10) 0.85216(8) 0.0608(4) Uani 1 1 d . . . . .
C14 C 0.23534(18) 0.00147(12) 0.85735(10) 0.0273(3) Uani 1 1 d . . . . .
H4B H 0.195(2) -0.0234(14) 0.8001(12) 0.024(4) Uiso 1 1 d . . . . .
C10 C 0.40870(19) 0.11954(12) 0.94968(9) 0.0269(3) Uani 1 1 d . . . . .
H5A H 0.489(3) 0.1737(16) 0.9582(13) 0.035(5) Uiso 1 1 d . . . . .
C11 C 0.3467(2) 0.08452(14) 1.02216(10) 0.0333(3) Uani 1 1 d . . . . .
H6A H 0.386(3) 0.1123(19) 1.0798(16) 0.053(7) Uiso 1 1 d . . . . .
C13 C 0.1743(2) -0.03340(14) 0.93082(12) 0.0341(3) Uani 1 1 d . . . . .
H7A H 0.098(3) -0.0862(18) 0.9232(14) 0.043(6) Uiso 1 1 d . . . . .
C6 C 0.79740(18) 0.24201(11) 0.75636(10) 0.0275(3) Uani 1 1 d . . . . .
H8A H 0.806(2) 0.2760(15) 0.7036(13) 0.031(5) Uiso 1 1 d . . . . .
C12 C 0.2305(2) 0.00821(14) 1.01285(11) 0.0361(4) Uani 1 1 d . . . . .
H9A H 0.189(3) -0.0160(18) 1.0652(16) 0.050(6) Uiso 1 1 d . . . . .
C3 C 0.2877(2) 0.12855(13) 0.55368(10) 0.0331(3) Uani 1 1 d . . . . .
H10A H 0.350(3) 0.1636(16) 0.5159(15) 0.039(6) Uiso 1 1 d . . . . .
C7 C 0.7954(2) 0.31660(15) 0.82938(13) 0.0388(4) Uani 1 1 d . . . . .
H11A H 0.703(3) 0.365(2) 0.8143(17) 0.059(7) Uiso 1 1 d . . . . .
H11B H 0.904(3) 0.3571(18) 0.8371(16) 0.051(6) Uiso 1 1 d . . . . .
H11C H 0.792(3) 0.2835(18) 0.8831(16) 0.046(6) Uiso 1 1 d . . . . .
C8 C 0.9351(2) 0.16511(16) 0.7775(2) 0.0500(5) Uani 1 1 d . . . . .
H12A H 0.925(3) 0.117(2) 0.7306(18) 0.061(8) Uiso 1 1 d . . . . .
H12B H 0.925(4) 0.129(2) 0.838(2) 0.078(9) Uiso 1 1 d . . . . .
H12C H 1.045(3) 0.200(2) 0.7871(17) 0.059(7) Uiso 1 1 d . . . . .
C4 C 0.1247(3) 0.1829(2) 0.55502(15) 0.0514(5) Uani 1 1 d . . . . .
H13A H 0.147(3) 0.247(2) 0.5783(18) 0.062(8) Uiso 1 1 d . . . . .
H13B H 0.058(3) 0.1450(19) 0.5895(17) 0.051(7) Uiso 1 1 d . . . . .
H13C H 0.068(3) 0.185(2) 0.4946(18) 0.063(7) Uiso 1 1 d . . . . .
C5 C 0.2650(4) 0.02069(16) 0.52782(13) 0.0493(5) Uani 1 1 d . . . . .
H14A H 0.377(4) -0.009(2) 0.5323(17) 0.060(8) Uiso 1 1 d . . . . .
H14B H 0.210(3) 0.018(2) 0.4653(19) 0.069(8) Uiso 1 1 d . . . . .
H14C H 0.190(3) -0.0111(19) 0.5623(17) 0.053(7) Uiso 1 1 d . . . . .
B1 B 0.2888(2) 0.38758(12) 0.77776(11) 0.0261(3) Uani 1 1 d . . . . .
C1 C 0.42035(17) 0.11429(10) 0.79028(8) 0.0214(2) 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
N3 N4 1.2913(16) . ?
N3 C2 1.4136(19) . ?
N3 C6 1.5021(19) . ?
O1 C2 1.2025(18) . ?
F1 B1 1.380(2) . ?
N1 N2 1.3072(16) . ?
N1 C2 1.3985(19) . ?
N1 C3 1.5044(19) . ?
C9 C14 1.393(2) . ?
C9 C10 1.399(2) . ?
C9 C1 1.4718(19) . ?
F2 B1 1.379(2) . ?
N2 C1 1.3401(17) . ?
F3 B1 1.386(2) . ?
N4 C1 1.3438(18) . ?
F4 B1 1.373(2) . ?
C14 C13 1.395(2) . ?
C14 H4B 0.950(19) . ?
C10 C11 1.386(2) . ?
C10 H5A 0.97(2) . ?
C11 C12 1.386(3) . ?
C11 H6A 0.97(2) . ?
C13 C12 1.389(3) . ?
C13 H7A 0.94(2) . ?
C6 C7 1.514(2) . ?
C6 C8 1.518(2) . ?
C6 H8A 0.95(2) . ?
C12 H9A 0.98(2) . ?
C3 C5 1.513(3) . ?
C3 C4 1.514(3) . ?
C3 H10A 0.96(2) . ?
C7 H11A 0.99(3) . ?
C7 H11B 1.02(2) . ?
C7 H11C 0.95(2) . ?
C8 H12A 0.96(3) . ?
C8 H12B 1.06(3) . ?
C8 H12C 0.99(3) . ?
C4 H13A 0.95(3) . ?
C4 H13B 0.97(3) . ?
C4 H13C 0.97(3) . ?
C5 H14A 0.99(3) . ?
C5 H14B 0.99(3) . ?
C5 H14C 0.97(3) . ?

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
N4 N3 C2 124.77(12) . . ?
N4 N3 C6 116.95(11) . . ?
C2 N3 C6 118.27(11) . . ?
N2 N1 C2 124.84(12) . . ?
N2 N1 C3 116.88(12) . . ?
C2 N1 C3 118.29(12) . . ?
C14 C9 C10 120.28(13) . . ?
C14 C9 C1 120.27(12) . . ?
C10 C9 C1 119.45(13) . . ?
N1 N2 C1 117.37(12) . . ?
O1 C2 N1 125.02(14) . . ?
O1 C2 N3 123.54(14) . . ?
N1 C2 N3 111.42(12) . . ?
N3 N4 C1 117.71(11) . . ?
C9 C14 C13 119.61(14) . . ?
C9 C14 H4B 118.8(11) . . ?
C13 C14 H4B 121.5(11) . . ?
C11 C10 C9 119.58(15) . . ?
C11 C10 H5A 118.3(12) . . ?
C9 C10 H5A 122.2(12) . . ?
C10 C11 C12 120.25(15) . . ?
C10 C11 H6A 120.3(15) . . ?
C12 C11 H6A 119.5(15) . . ?
C12 C13 C14 119.88(16) . . ?
C12 C13 H7A 121.9(13) . . ?
C14 C13 H7A 118.2(13) . . ?
N3 C6 C7 109.35(13) . . ?
N3 C6 C8 108.47(13) . . ?
C7 C6 C8 113.33(17) . . ?
N3 C6 H8A 105.2(12) . . ?
C7 C6 H8A 109.2(12) . . ?
C8 C6 H8A 111.0(12) . . ?
C11 C12 C13 120.40(14) . . ?
C11 C12 H9A 118.9(14) . . ?
C13 C12 H9A 120.7(14) . . ?
N1 C3 C5 109.20(14) . . ?
N1 C3 C4 108.91(14) . . ?
C5 C3 C4 113.77(18) . . ?
N1 C3 H10A 104.2(13) . . ?
C5 C3 H10A 111.6(13) . . ?
C4 C3 H10A 108.7(13) . . ?
C6 C7 H11A 111.8(15) . . ?
C6 C7 H11B 108.9(14) . . ?
H11A C7 H11B 105(2) . . ?
C6 C7 H11C 110.1(15) . . ?
H11A C7 H11C 113(2) . . ?
H11B C7 H11C 107.8(19) . . ?
C6 C8 H12A 109.4(16) . . ?
C6 C8 H12B 109.7(17) . . ?
H12A C8 H12B 110(2) . . ?
C6 C8 H12C 108.4(16) . . ?
H12A C8 H12C 113(2) . . ?
H12B C8 H12C 106(2) . . ?
C3 C4 H13A 110.0(17) . . ?
C3 C4 H13B 109.0(15) . . ?
H13A C4 H13B 111(2) . . ?
C3 C4 H13C 105.7(16) . . ?
H13A C4 H13C 111(2) . . ?
H13B C4 H13C 109(2) . . ?
C3 C5 H14A 107.7(16) . . ?
C3 C5 H14B 107.5(17) . . ?
H14A C5 H14B 108(2) . . ?
C3 C5 H14C 109.8(15) . . ?
H14A C5 H14C 116(2) . . ?
H14B C5 H14C 107(2) . . ?
F4 B1 F2 110.98(14) . . ?
F4 B1 F1 110.31(15) . . ?
F2 B1 F1 109.69(15) . . ?
F4 B1 F3 108.19(14) . . ?
F2 B1 F3 109.51(14) . . ?
F1 B1 F3 108.10(14) . . ?
N2 C1 N4 123.17(12) . . ?
N2 C1 C9 119.30(12) . . ?
N4 C1 C9 117.50(11) . . ?

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
C2 N1 N2 C1 3.1(2) . . . . ?
C3 N1 N2 C1 -177.22(13) . . . . ?
N2 N1 C2 O1 173.07(15) . . . . ?
C3 N1 C2 O1 -6.6(2) . . . . ?
N2 N1 C2 N3 -8.76(19) . . . . ?
C3 N1 C2 N3 171.56(12) . . . . ?
N4 N3 C2 O1 -172.97(14) . . . . ?
C6 N3 C2 O1 5.5(2) . . . . ?
N4 N3 C2 N1 8.83(19) . . . . ?
C6 N3 C2 N1 -172.66(12) . . . . ?
C2 N3 N4 C1 -3.18(19) . . . . ?
C6 N3 N4 C1 178.30(12) . . . . ?
C10 C9 C14 C13 -0.7(2) . . . . ?
C1 C9 C14 C13 179.24(14) . . . . ?
C14 C9 C10 C11 0.5(2) . . . . ?
C1 C9 C10 C11 -179.48(13) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C9 C14 C13 C12 0.4(2) . . . . ?
N4 N3 C6 C7 -45.06(17) . . . . ?
C2 N3 C6 C7 136.32(15) . . . . ?
N4 N3 C6 C8 78.98(18) . . . . ?
C2 N3 C6 C8 -99.65(17) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C14 C13 C12 C11 0.2(3) . . . . ?
N2 N1 C3 C5 -69.2(2) . . . . ?
C2 N1 C3 C5 110.54(17) . . . . ?
N2 N1 C3 C4 55.61(19) . . . . ?
C2 N1 C3 C4 -124.68(17) . . . . ?
N1 N2 C1 N4 3.8(2) . . . . ?
N1 N2 C1 C9 -178.24(12) . . . . ?
N3 N4 C1 N2 -3.8(2) . . . . ?
N3 N4 C1 C9 178.26(12) . . . . ?
C14 C9 C1 N2 25.4(2) . . . . ?
C10 C9 C1 N2 -154.62(13) . . . . ?
C14 C9 C1 N4 -156.52(13) . . . . ?
C10 C9 C1 N4 23.44(19) . . . . ?

_refine_diff_density_max         0.868
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 991916'
