# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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.
#
#  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_tt
_audit_creation_date             2014-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         
'2(C7 H7 O3 S), 2(C17 H20 N O2), 2(H2 O), O, C2 H3 N'
_chemical_formula_sum            'C50 H63 N3 O13 S2'
_chemical_formula_weight         978.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
S S 0.1246 0.1234 '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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.6904(6)
_cell_length_b                   21.8223(8)
_cell_length_c                   15.8024(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.2560(10)
_cell_angle_gamma                90.00
_cell_volume                     4971.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.9243
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1608
_diffrn_reflns_av_unetI/netI     0.2023
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            39135
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.55
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4480
_reflns_number_total             11991
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.865
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         11991
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2219
_refine_ls_R_factor_gt           0.0752
_refine_ls_restrained_S_all      0.865
_refine_ls_shift/su_max          0.189
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0689P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1510
_refine_ls_wR_factor_ref         0.1891
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Sof(O4W)=Sof(H4WA)=Sof(H4WB)=1-FVAR(1)
 Sof(O3W)=Sof(H3WA)=Sof(H3WB)=FVAR(1)
3.a Free rotating group:
 O1W(H1WA,H1WB), O3W(H3WA,H3WB), O4W(H4WA,H4WB)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C16'(H16C,H16D)
3.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C2A'(H2A'), C3A'(H3A'), C5A'(H5A'),
 C6A'(H6A'), C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10),
 C13(H13), C1'(H1'), C2'(H2'), C4'(H4'), C5'(H5'), C6'(H6'), C7'(H7'), C9'(H9'),
  C10'(H10'), C13'(H13')
3.d Idealised Me refined as rotating group:
 C7A(H7AA,H7AB,H7AC), C7A'(H7AD,H7AE,H7AF), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C17(H17A,H17B,H17C), C14'(H14D,H14E,H14F), C15'(H15D,H15E,H15F),
 C17'(H17D,H17E,H17F), C2S(H2SA,H2SB,H2SC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.22751(8) 0.12460(5) 0.88826(7) 0.0285(3) Uani 1 1 d . . .
O11 O 0.15526(19) 0.16142(12) 0.90103(19) 0.0329(7) Uani 1 1 d . . .
O12 O 0.2828(2) 0.15971(13) 0.8507(2) 0.0391(8) Uani 1 1 d . . .
O13 O 0.1902(2) 0.06800(12) 0.83776(19) 0.0364(8) Uani 1 1 d . . .
C1A C 0.3027(3) 0.10258(17) 1.0009(3) 0.0243(9) Uani 1 1 d . . .
C2A C 0.2673(3) 0.07317(17) 1.0575(3) 0.0287(10) Uani 1 1 d . . .
H2A H 0.2037 0.0618 1.0337 0.034 Uiso 1 1 calc . . R
C3A C 0.3229(3) 0.06014(18) 1.1478(3) 0.0308(10) Uani 1 1 d . . .
H3A H 0.2968 0.0408 1.1859 0.037 Uiso 1 1 calc . . R
C4A C 0.4163(3) 0.07480(17) 1.1838(3) 0.0298(10) Uani 1 1 d . . .
C5A C 0.4513(3) 0.10298(19) 1.1264(3) 0.0355(11) Uani 1 1 d . . .
H5A H 0.5154 0.1127 1.1496 0.043 Uiso 1 1 calc . . R
C6A C 0.3955(3) 0.11764(19) 1.0355(3) 0.0345(11) Uani 1 1 d . . .
H6A H 0.4212 0.1378 0.9977 0.041 Uiso 1 1 calc . . R
C7A C 0.4763(3) 0.0595(2) 1.2829(3) 0.0417(12) Uani 1 1 d . . .
H7AA H 0.4523 0.0806 1.3237 0.063 Uiso 1 1 calc . . GR
H7AB H 0.5401 0.0729 1.2971 0.063 Uiso 1 1 calc . . GR
H7AC H 0.4754 0.0152 1.2923 0.063 Uiso 1 1 calc . . GR
S2 S 0.23284(8) 0.12533(5) 0.38734(8) 0.0335(3) Uani 1 1 d . . .
O21 O 0.2179(2) 0.19054(12) 0.3817(2) 0.0461(9) Uani 1 1 d . . .
O22 O 0.1486(2) 0.08968(15) 0.3543(2) 0.0593(11) Uani 1 1 d . . .
O23 O 0.2963(2) 0.10636(15) 0.3448(2) 0.0555(10) Uani 1 1 d . . .
C1A' C 0.2910(3) 0.10847(16) 0.5065(3) 0.0255(9) Uani 1 1 d . . .
C2A' C 0.2406(3) 0.09583(17) 0.5598(3) 0.0300(10) Uani 1 1 d . . .
H2A' H 0.1747 0.0953 0.5324 0.036 Uiso 1 1 calc . . R
C3A' C 0.2871(3) 0.08394(17) 0.6535(3) 0.0305(10) Uani 1 1 d . . .
H3A' H 0.2523 0.0753 0.6895 0.037 Uiso 1 1 calc . . R
C4A' C 0.3824(3) 0.08451(17) 0.6949(3) 0.0310(10) Uani 1 1 d . . .
C5A' C 0.4318(3) 0.09863(17) 0.6409(3) 0.0331(11) Uani 1 1 d . . .
H5A' H 0.4977 0.0999 0.6688 0.040 Uiso 1 1 calc . . R
C6A' C 0.3871(3) 0.11089(17) 0.5477(3) 0.0272(10) Uani 1 1 d . . .
H6A' H 0.4219 0.1209 0.5123 0.033 Uiso 1 1 calc . . R
C7A' C 0.4322(4) 0.0693(2) 0.7960(3) 0.0481(13) Uani 1 1 d . . .
H7AD H 0.4055 0.0933 0.8319 0.072 Uiso 1 1 calc . . GR
H7AE H 0.4982 0.0791 0.8161 0.072 Uiso 1 1 calc . . GR
H7AF H 0.4251 0.0255 0.8055 0.072 Uiso 1 1 calc . . GR
O1 O 0.1432(2) 0.40709(12) 0.07530(18) 0.0327(7) Uani 1 1 d . . .
O2 O 0.11109(18) 0.30625(12) 0.13864(18) 0.0281(7) Uani 1 1 d . . .
N1 N 0.4158(2) 0.28456(14) 0.7882(2) 0.0250(8) Uani 1 1 d . . .
C1 C 0.3558(3) 0.24468(18) 0.7290(3) 0.0278(10) Uani 1 1 d . . .
H1 H 0.3380 0.2090 0.7523 0.033 Uiso 1 1 calc . . R
C2 C 0.3207(3) 0.25472(18) 0.6371(3) 0.0261(9) Uani 1 1 d . . .
H2 H 0.2801 0.2252 0.5969 0.031 Uiso 1 1 calc . . R
C3 C 0.3426(3) 0.30750(17) 0.5999(3) 0.0242(9) Uani 1 1 d . . .
C4 C 0.4055(3) 0.34798(18) 0.6637(3) 0.0287(10) Uani 1 1 d . . .
H4 H 0.4230 0.3846 0.6422 0.034 Uiso 1 1 calc . . R
C5 C 0.4417(3) 0.33569(18) 0.7556(3) 0.0302(10) Uani 1 1 d . . .
H5 H 0.4853 0.3631 0.7972 0.036 Uiso 1 1 calc . . R
C6 C 0.3013(3) 0.31753(17) 0.5016(3) 0.0254(9) Uani 1 1 d . . .
H6 H 0.2607 0.2865 0.4654 0.031 Uiso 1 1 calc . . R
C7 C 0.3143(3) 0.36604(17) 0.4563(3) 0.0274(10) Uani 1 1 d . . .
H7 H 0.3556 0.3968 0.4923 0.033 Uiso 1 1 calc . . R
C8 C 0.2714(3) 0.37637(17) 0.3577(3) 0.0216(8) Uani 1 1 d . . .
C9 C 0.2901(3) 0.42975(17) 0.3208(3) 0.0272(10) Uani 1 1 d . . .
H9 H 0.3320 0.4587 0.3606 0.033 Uiso 1 1 calc . . R
C10 C 0.2491(3) 0.44195(17) 0.2268(3) 0.0280(10) Uani 1 1 d . . .
H10 H 0.2624 0.4791 0.2032 0.034 Uiso 1 1 calc . . R
C11 C 0.1892(3) 0.40011(17) 0.1681(3) 0.0262(9) Uani 1 1 d . . .
C12 C 0.1705(3) 0.34462(17) 0.2037(3) 0.0226(9) Uani 1 1 d . . .
C13 C 0.2106(3) 0.33336(17) 0.2966(3) 0.0253(9) Uani 1 1 d . . .
H13 H 0.1973 0.2962 0.3202 0.030 Uiso 1 1 calc . . R
C14 C 0.1542(3) 0.46483(18) 0.0366(3) 0.0441(13) Uani 1 1 d . . .
H14A H 0.1156 0.4652 -0.0296 0.066 Uiso 1 1 calc . . GR
H14B H 0.2194 0.4703 0.0463 0.066 Uiso 1 1 calc . . GR
H14C H 0.1351 0.4982 0.0667 0.066 Uiso 1 1 calc . . GR
C15 C 0.0822(3) 0.25247(18) 0.1706(3) 0.0331(11) Uani 1 1 d . . .
H15A H 0.0375 0.2301 0.1181 0.050 Uiso 1 1 calc . . GR
H15B H 0.0531 0.2639 0.2129 0.050 Uiso 1 1 calc . . GR
H15C H 0.1362 0.2264 0.2028 0.050 Uiso 1 1 calc . . GR
C16 C 0.4563(3) 0.27006(19) 0.8880(3) 0.0324(10) Uani 1 1 d . . .
H16A H 0.4096 0.2485 0.9047 0.039 Uiso 1 1 calc . . R
H16B H 0.4733 0.3086 0.9239 0.039 Uiso 1 1 calc . . R
C17 C 0.5416(3) 0.2301(2) 0.9121(3) 0.0387(12) Uani 1 1 d . . .
H17A H 0.5257 0.1933 0.8734 0.058 Uiso 1 1 calc . . GR
H17B H 0.5641 0.2182 0.9771 0.058 Uiso 1 1 calc . . GR
H17C H 0.5901 0.2530 0.9013 0.058 Uiso 1 1 calc . . GR
O3 O 0.15756(19) 0.38937(12) -0.41671(19) 0.0299(7) Uani 1 1 d . . .
O4 O 0.12451(18) 0.28666(12) -0.35847(18) 0.0287(7) Uani 1 1 d . . .
N2 N 0.3933(2) 0.25917(15) 0.2920(2) 0.0263(8) Uani 1 1 d . . .
C1' C 0.3372(3) 0.21848(18) 0.2315(3) 0.0273(10) Uani 1 1 d . . .
H1' H 0.3232 0.1807 0.2530 0.033 Uiso 1 1 calc . . R
C2' C 0.3004(3) 0.23127(18) 0.1397(3) 0.0287(10) Uani 1 1 d . . .
H2' H 0.2606 0.2024 0.0975 0.034 Uiso 1 1 calc . . R
C3' C 0.3208(3) 0.28678(17) 0.1070(3) 0.0242(9) Uani 1 1 d . . .
C4' C 0.3790(3) 0.32764(18) 0.1715(3) 0.0269(10) Uani 1 1 d . . .
H4' H 0.3944 0.3657 0.1521 0.032 Uiso 1 1 calc . . R
C5' C 0.4139(3) 0.31299(19) 0.2631(3) 0.0284(10) Uani 1 1 d . . .
H5' H 0.4532 0.3412 0.3070 0.034 Uiso 1 1 calc . . R
C6' C 0.2832(3) 0.29756(18) 0.0072(3) 0.0259(9) Uani 1 1 d . . .
H6' H 0.2512 0.2645 -0.0313 0.031 Uiso 1 1 calc . . R
C7' C 0.2897(3) 0.34964(18) -0.0345(3) 0.0278(10) Uani 1 1 d . . .
H7' H 0.3210 0.3827 0.0044 0.033 Uiso 1 1 calc . . R
C8' C 0.2535(3) 0.36103(17) -0.1339(3) 0.0272(10) Uani 1 1 d . . .
C9' C 0.2673(3) 0.41713(18) -0.1671(3) 0.0311(10) Uani 1 1 d . . .
H9' H 0.2981 0.4486 -0.1244 0.037 Uiso 1 1 calc . . R
C10' C 0.2377(3) 0.42892(18) -0.2601(3) 0.0265(9) Uani 1 1 d . . .
H10' H 0.2493 0.4677 -0.2808 0.032 Uiso 1 1 calc . . R
C11' C 0.1909(3) 0.38387(17) -0.3231(3) 0.0243(9) Uani 1 1 d . . .
C12' C 0.1740(3) 0.32675(17) -0.2909(3) 0.0237(9) Uani 1 1 d . . .
C13' C 0.2050(3) 0.31549(17) -0.1983(3) 0.0254(9) Uani 1 1 d . . .
H13' H 0.1938 0.2767 -0.1773 0.030 Uiso 1 1 calc . . R
C14' C 0.1702(3) 0.44676(18) -0.4529(3) 0.0387(12) Uani 1 1 d . . .
H14D H 0.1440 0.4448 -0.5203 0.058 Uiso 1 1 calc . . GR
H14E H 0.2366 0.4561 -0.4303 0.058 Uiso 1 1 calc . . GR
H14F H 0.1387 0.4789 -0.4329 0.058 Uiso 1 1 calc . . GR
C15' C 0.0975(3) 0.23001(19) -0.3299(3) 0.0470(14) Uani 1 1 d . . .
H15D H 0.0564 0.2073 -0.3842 0.070 Uiso 1 1 calc . . GR
H15E H 0.0649 0.2387 -0.2896 0.070 Uiso 1 1 calc . . GR
H15F H 0.1529 0.2054 -0.2964 0.070 Uiso 1 1 calc . . GR
C16' C 0.4381(3) 0.24251(19) 0.3913(3) 0.0335(11) Uani 1 1 d . . .
H16C H 0.3978 0.2138 0.4071 0.040 Uiso 1 1 calc . . R
H16D H 0.4467 0.2798 0.4296 0.040 Uiso 1 1 calc . . R
C17' C 0.5306(3) 0.21307(19) 0.4111(3) 0.0365(11) Uani 1 1 d . . .
H17D H 0.5222 0.1772 0.3713 0.055 Uiso 1 1 calc . . GR
H17E H 0.5583 0.2002 0.4758 0.055 Uiso 1 1 calc . . GR
H17F H 0.5717 0.2426 0.3993 0.055 Uiso 1 1 calc . . GR
O1W O 0.0872(2) 0.06851(15) 0.1552(2) 0.0494(9) Uani 1 1 d . . .
H1WA H 0.1141 0.0767 0.2138 0.074 Uiso 1 1 d . . G
H1WB H 0.0419 0.0429 0.1458 0.074 Uiso 1 1 d . . G
O2W O 0.0379(2) 0.12448(16) 0.9873(2) 0.0535(9) Uani 1 1 d . . .
O3W O -0.0489(18) -0.0101(15) 0.110(2) 0.051(5) Uani 0.36(6) 1 d A 1 .
H3WA H -0.0392 -0.0190 0.0608 0.077 Uiso 0.36(6) 1 d A 1 G
H3WB H -0.1043 -0.0221 0.1027 0.077 Uiso 0.36(6) 1 d A 1 G
O4W O -0.0248(19) -0.0345(17) 0.139(2) 0.082(6) Uani 0.64(6) 1 d A 2 .
H4WA H -0.0502 -0.0540 0.1712 0.123 Uiso 0.64(6) 1 d A 2 G
H4WB H -0.0233 -0.0582 0.0954 0.123 Uiso 0.64(6) 1 d A 2 G
N1S N 0.5042(4) 0.4128(2) 0.0329(4) 0.0863(17) Uani 1 1 d . . .
C1S C 0.5119(4) 0.4491(3) 0.0895(5) 0.0690(18) Uani 1 1 d . . .
C2S C 0.5105(5) 0.4949(3) 0.1525(5) 0.099(2) Uani 1 1 d . . .
H2SA H 0.5158 0.5354 0.1281 0.148 Uiso 1 1 calc . . GR
H2SB H 0.5626 0.4886 0.2118 0.148 Uiso 1 1 calc . . GR
H2SC H 0.4520 0.4925 0.1610 0.148 Uiso 1 1 calc . . GR


_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
S1 O11 1.467(3) . ?
S1 O12 1.449(3) . ?
S1 O13 1.461(3) . ?
S1 C1A 1.770(4) . ?
C1A C2A 1.383(5) . ?
C1A C6A 1.378(5) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.376(5) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.384(5) . ?
C4A C5A 1.376(6) . ?
C4A C7A 1.512(6) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.393(6) . ?
C6A H6A 0.9500 . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?
S2 O21 1.439(3) . ?
S2 O22 1.442(3) . ?
S2 O23 1.463(3) . ?
S2 C1A' 1.777(4) . ?
C1A' C2A' 1.392(6) . ?
C1A' C6A' 1.387(6) . ?
C2A' H2A' 0.9500 . ?
C2A' C3A' 1.392(6) . ?
C3A' H3A' 0.9500 . ?
C3A' C4A' 1.376(6) . ?
C4A' C5A' 1.395(6) . ?
C4A' C7A' 1.513(6) . ?
C5A' H5A' 0.9500 . ?
C5A' C6A' 1.385(6) . ?
C6A' H6A' 0.9500 . ?
C7A' H7AD 0.9800 . ?
C7A' H7AE 0.9800 . ?
C7A' H7AF 0.9800 . ?
O1 C11 1.364(5) . ?
O1 C14 1.440(5) . ?
O2 C12 1.368(4) . ?
O2 C15 1.420(4) . ?
N1 C1 1.350(5) . ?
N1 C5 1.356(5) . ?
N1 C16 1.484(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.352(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(5) . ?
C3 C4 1.409(5) . ?
C3 C6 1.444(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.361(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.338(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.451(5) . ?
C8 C9 1.386(5) . ?
C8 C13 1.412(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.374(5) . ?
C11 C12 1.413(5) . ?
C12 C13 1.372(5) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.515(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O3 C11' 1.365(5) . ?
O3 C14' 1.423(5) . ?
O4 C12' 1.361(4) . ?
O4 C15' 1.436(5) . ?
N2 C1' 1.346(5) . ?
N2 C5' 1.345(5) . ?
N2 C16' 1.490(5) . ?
C1' H1' 0.9500 . ?
C1' C2' 1.362(5) . ?
C2' H2' 0.9500 . ?
C2' C3' 1.403(5) . ?
C3' C4' 1.391(5) . ?
C3' C6' 1.467(5) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.368(5) . ?
C5' H5' 0.9500 . ?
C6' H6' 0.9500 . ?
C6' C7' 1.338(5) . ?
C7' H7' 0.9500 . ?
C7' C8' 1.465(6) . ?
C8' C9' 1.382(5) . ?
C8' C13' 1.410(5) . ?
C9' H9' 0.9500 . ?
C9' C10' 1.380(6) . ?
C10' H10' 0.9500 . ?
C10' C11' 1.386(5) . ?
C11' C12' 1.411(5) . ?
C12' C13' 1.370(5) . ?
C13' H13' 0.9500 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?
C15' H15D 0.9800 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9800 . ?
C16' H16C 0.9900 . ?
C16' H16D 0.9900 . ?
C16' C17' 1.502(6) . ?
C17' H17D 0.9800 . ?
C17' H17E 0.9800 . ?
C17' H17F 0.9800 . ?
O1W H1WA 0.8700 . ?
O1W H1WB 0.8699 . ?
O3W H3WA 0.8700 . ?
O3W H3WB 0.8700 . ?
O3W H4WA 1.3672 . ?
O4W H3WA 1.2138 . ?
O4W H4WA 0.8699 . ?
O4W H4WB 0.8701 . ?
N1S C1S 1.164(7) . ?
C1S C2S 1.418(8) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 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
O11 S1 C1A 104.76(18) . . ?
O12 S1 O11 112.77(17) . . ?
O12 S1 O13 113.48(18) . . ?
O12 S1 C1A 106.65(18) . . ?
O13 S1 O11 111.93(17) . . ?
O13 S1 C1A 106.49(17) . . ?
C2A C1A S1 119.8(3) . . ?
C6A C1A S1 120.9(3) . . ?
C6A C1A C2A 119.1(4) . . ?
C1A C2A H2A 119.5 . . ?
C3A C2A C1A 120.9(4) . . ?
C3A C2A H2A 119.5 . . ?
C2A C3A H3A 119.6 . . ?
C2A C3A C4A 120.9(4) . . ?
C4A C3A H3A 119.6 . . ?
C3A C4A C7A 120.0(4) . . ?
C5A C4A C3A 117.7(4) . . ?
C5A C4A C7A 122.2(4) . . ?
C4A C5A H5A 118.9 . . ?
C4A C5A C6A 122.1(4) . . ?
C6A C5A H5A 118.9 . . ?
C1A C6A C5A 119.2(4) . . ?
C1A C6A H6A 120.4 . . ?
C5A C6A H6A 120.4 . . ?
C4A C7A H7AA 109.5 . . ?
C4A C7A H7AB 109.5 . . ?
C4A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
O21 S2 O22 114.0(2) . . ?
O21 S2 O23 112.0(2) . . ?
O21 S2 C1A' 105.87(18) . . ?
O22 S2 O23 111.9(2) . . ?
O22 S2 C1A' 106.64(19) . . ?
O23 S2 C1A' 105.7(2) . . ?
C2A' C1A' S2 120.3(3) . . ?
C6A' C1A' S2 119.9(3) . . ?
C6A' C1A' C2A' 119.7(4) . . ?
C1A' C2A' H2A' 120.1 . . ?
C1A' C2A' C3A' 119.7(4) . . ?
C3A' C2A' H2A' 120.1 . . ?
C2A' C3A' H3A' 119.4 . . ?
C4A' C3A' C2A' 121.3(4) . . ?
C4A' C3A' H3A' 119.4 . . ?
C3A' C4A' C5A' 118.3(4) . . ?
C3A' C4A' C7A' 120.8(4) . . ?
C5A' C4A' C7A' 120.9(4) . . ?
C4A' C5A' H5A' 119.3 . . ?
C6A' C5A' C4A' 121.5(4) . . ?
C6A' C5A' H5A' 119.3 . . ?
C1A' C6A' H6A' 120.2 . . ?
C5A' C6A' C1A' 119.5(4) . . ?
C5A' C6A' H6A' 120.2 . . ?
C4A' C7A' H7AD 109.5 . . ?
C4A' C7A' H7AE 109.5 . . ?
C4A' C7A' H7AF 109.5 . . ?
H7AD C7A' H7AE 109.5 . . ?
H7AD C7A' H7AF 109.5 . . ?
H7AE C7A' H7AF 109.5 . . ?
C11 O1 C14 117.0(3) . . ?
C12 O2 C15 117.2(3) . . ?
C1 N1 C5 120.0(3) . . ?
C1 N1 C16 119.2(3) . . ?
C5 N1 C16 120.8(3) . . ?
N1 C1 H1 119.5 . . ?
N1 C1 C2 121.1(4) . . ?
C2 C1 H1 119.5 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.4(4) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 115.8(4) . . ?
C2 C3 C6 119.8(4) . . ?
C4 C3 C6 124.4(4) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.3(4) . . ?
C5 C4 H4 119.4 . . ?
N1 C5 H5 119.8 . . ?
C4 C5 N1 120.4(4) . . ?
C4 C5 H5 119.8 . . ?
C3 C6 H6 116.7 . . ?
C7 C6 C3 126.6(4) . . ?
C7 C6 H6 116.7 . . ?
C6 C7 H7 116.8 . . ?
C6 C7 C8 126.4(4) . . ?
C8 C7 H7 116.8 . . ?
C9 C8 C7 119.8(4) . . ?
C9 C8 C13 118.0(4) . . ?
C13 C8 C7 122.2(4) . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.6(4) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.9(4) . . ?
C11 C10 H10 120.1 . . ?
O1 C11 C10 125.6(4) . . ?
O1 C11 C12 114.8(3) . . ?
C10 C11 C12 119.7(4) . . ?
O2 C12 C11 114.3(3) . . ?
O2 C12 C13 125.7(4) . . ?
C13 C12 C11 120.0(4) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.8(4) . . ?
C12 C13 H13 119.6 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 C17 110.8(3) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11' O3 C14' 117.3(3) . . ?
C12' O4 C15' 117.0(3) . . ?
C1' N2 C16' 119.4(3) . . ?
C5' N2 C1' 120.9(4) . . ?
C5' N2 C16' 119.6(3) . . ?
N2 C1' H1' 119.9 . . ?
N2 C1' C2' 120.3(4) . . ?
C2' C1' H1' 119.9 . . ?
C1' C2' H2' 119.8 . . ?
C1' C2' C3' 120.5(4) . . ?
C3' C2' H2' 119.8 . . ?
C2' C3' C6' 118.7(4) . . ?
C4' C3' C2' 117.5(4) . . ?
C4' C3' C6' 123.7(4) . . ?
C3' C4' H4' 120.0 . . ?
C5' C4' C3' 120.0(4) . . ?
C5' C4' H4' 120.0 . . ?
N2 C5' C4' 120.9(4) . . ?
N2 C5' H5' 119.6 . . ?
C4' C5' H5' 119.6 . . ?
C3' C6' H6' 117.0 . . ?
C7' C6' C3' 126.1(4) . . ?
C7' C6' H6' 117.0 . . ?
C6' C7' H7' 116.6 . . ?
C6' C7' C8' 126.9(4) . . ?
C8' C7' H7' 116.6 . . ?
C9' C8' C7' 120.3(4) . . ?
C9' C8' C13' 118.1(4) . . ?
C13' C8' C7' 121.6(4) . . ?
C8' C9' H9' 118.9 . . ?
C8' C9' C10' 122.1(4) . . ?
C10' C9' H9' 118.9 . . ?
C9' C10' H10' 120.2 . . ?
C11' C10' C9' 119.6(4) . . ?
C11' C10' H10' 120.2 . . ?
O3 C11' C10' 125.7(4) . . ?
O3 C11' C12' 115.0(3) . . ?
C10' C11' C12' 119.3(4) . . ?
O4 C12' C11' 114.5(3) . . ?
O4 C12' C13' 125.1(4) . . ?
C13' C12' C11' 120.4(4) . . ?
C8' C13' H13' 119.8 . . ?
C12' C13' C8' 120.5(4) . . ?
C12' C13' H13' 119.8 . . ?
O3 C14' H14D 109.5 . . ?
O3 C14' H14E 109.5 . . ?
O3 C14' H14F 109.5 . . ?
H14D C14' H14E 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
O4 C15' H15D 109.5 . . ?
O4 C15' H15E 109.5 . . ?
O4 C15' H15F 109.5 . . ?
H15D C15' H15E 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
N2 C16' H16C 109.7 . . ?
N2 C16' H16D 109.7 . . ?
N2 C16' C17' 109.9(3) . . ?
H16C C16' H16D 108.2 . . ?
C17' C16' H16C 109.7 . . ?
C17' C16' H16D 109.7 . . ?
C16' C17' H17D 109.5 . . ?
C16' C17' H17E 109.5 . . ?
C16' C17' H17F 109.5 . . ?
H17D C17' H17E 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
H1WA O1W H1WB 109.5 . . ?
H4WA O4W H4WB 109.5 . . ?
N1S C1S C2S 173.4(8) . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?

_database_code_depnum_ccdc_archive 'CCDC 969548'
#######################################################################
#
#                 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_p21c
_audit_creation_date             2014-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H20 N O2, B F4'
_chemical_formula_sum            'C17 H20 B F4 N O2'
_chemical_formula_weight         357.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.3589(3)
_cell_length_b                   20.8300(9)
_cell_length_c                   11.2706(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.727(3)
_cell_angle_gamma                90.00
_cell_volume                     1726.84(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3111
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      29.40
_cell_measurement_theta_min      2.66
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.298063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.2520 before and 0.0634 after correction.
The Ratio of minimum to maximum transmission is 0.2981.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            brightly-yel
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12462
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.96
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2314
_reflns_number_total             4142
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4142
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1481
_refine_ls_R_factor_gt           0.0790
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0878P)²+0.3163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1786
_refine_ls_wR_factor_ref         0.2012
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 B1-F1B \\sim B1-F2B \\sim B1-F3B \\sim B1-F4B
 with sigma of 0.01
3. Others
 Fixed Sof: F1(0.44586) F2(0.44586) F3(0.44586) F4(0.44586) F1A(0.47256)
 F2A(0.47256) F3A(0.47256) F4A(0.47256) F1B(0.08158) F2B(0.08158) F3B(0.08158)
 F4B(0.08158)
 Fixed Uiso: F3B(0.03574)
4.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
4.b Me refined with riding coordinates:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.1237(3) 0.36349(9) 0.88162(17) 0.0361(5) Uani 1 1 d . . .
O2 O 0.0943(3) 0.25647(8) 0.76344(17) 0.0361(5) Uani 1 1 d . . .
N1 N 0.3024(3) 0.66498(10) 0.20495(19) 0.0301(5) Uani 1 1 d . . .
C1 C 0.3019(4) 0.66815(13) 0.3245(2) 0.0321(6) Uani 1 1 d . . .
H1 H 0.3048 0.7090 0.3621 0.039 Uiso 1 1 calc . . R
C2 C 0.2974(4) 0.61365(12) 0.3932(2) 0.0313(6) Uani 1 1 d . . .
H2 H 0.2968 0.6169 0.4773 0.038 Uiso 1 1 calc . . R
C3 C 0.2935(4) 0.55272(12) 0.3378(2) 0.0317(6) Uani 1 1 d . . .
C4 C 0.3034(4) 0.55168(13) 0.2143(2) 0.0360(7) Uani 1 1 d . . .
H4 H 0.3079 0.5116 0.1742 0.043 Uiso 1 1 calc . . R
C5 C 0.3065(4) 0.60752(13) 0.1501(3) 0.0358(7) Uani 1 1 d . . .
H5 H 0.3117 0.6057 0.0660 0.043 Uiso 1 1 calc . . R
C6 C 0.2747(4) 0.49232(13) 0.4019(3) 0.0359(7) Uani 1 1 d . . .
H6 H 0.2862 0.4540 0.3570 0.043 Uiso 1 1 calc . . R
C7 C 0.2431(4) 0.48552(13) 0.5170(2) 0.0320(6) Uani 1 1 d . . .
H7 H 0.2400 0.5235 0.5635 0.038 Uiso 1 1 calc . . R
C8 C 0.2126(4) 0.42448(12) 0.5783(2) 0.0305(6) Uani 1 1 d . . .
C9 C 0.1891(4) 0.42432(12) 0.7017(2) 0.0286(6) Uani 1 1 d . . .
H9 H 0.1987 0.4635 0.7446 0.034 Uiso 1 1 calc . . R
C10 C 0.1519(4) 0.36770(12) 0.7620(2) 0.0283(6) Uani 1 1 d . . .
C11 C 0.1369(4) 0.30956(12) 0.6978(2) 0.0308(6) Uani 1 1 d . . .
C12 C 0.1642(4) 0.30941(13) 0.5770(3) 0.0341(7) Uani 1 1 d . . .
H12 H 0.1575 0.2702 0.5341 0.041 Uiso 1 1 calc . . R
C13 C 0.2013(4) 0.36601(13) 0.5177(3) 0.0361(7) Uani 1 1 d . . .
H13 H 0.2194 0.3650 0.4347 0.043 Uiso 1 1 calc . . R
C14 C 0.1511(5) 0.42156(14) 0.9493(3) 0.0441(8) Uani 1 1 d . . .
H14A H 0.1272 0.4132 1.0329 0.066 Uiso 1 1 calc . . R
H14B H 0.0678 0.4548 0.9190 0.066 Uiso 1 1 calc . . R
H14C H 0.2768 0.4362 0.9420 0.066 Uiso 1 1 calc . . R
C15 C 0.0908(5) 0.19597(13) 0.7008(3) 0.0466(8) Uani 1 1 d . . .
H15A H 0.0594 0.1614 0.7555 0.070 Uiso 1 1 calc . . R
H15B H 0.2107 0.1876 0.6686 0.070 Uiso 1 1 calc . . R
H15C H -0.0003 0.1979 0.6356 0.070 Uiso 1 1 calc . . R
C16 C 0.3043(4) 0.72509(13) 0.1330(2) 0.0335(7) Uani 1 1 d . . .
H16A H 0.2463 0.7602 0.1774 0.040 Uiso 1 1 calc . . R
H16B H 0.2332 0.7184 0.0580 0.040 Uiso 1 1 calc . . R
C17 C 0.4949(4) 0.74394(15) 0.1053(3) 0.0457(8) Uani 1 1 d . . .
H17A H 0.4927 0.7835 0.0583 0.069 Uiso 1 1 calc . . R
H17B H 0.5516 0.7096 0.0600 0.069 Uiso 1 1 calc . . R
H17C H 0.5649 0.7511 0.1795 0.069 Uiso 1 1 calc . . R
B1 B 0.3640(5) 0.61289(15) 0.8089(3) 0.0358(8) Uani 1 1 d . . .
F1 F 0.3788(7) 0.6757(2) 0.8585(4) 0.0276(11) Uiso 0.45 1 d A 1 .
F2 F 0.3408(9) 0.6173(2) 0.6891(4) 0.0359(11) Uiso 0.45 1 d A 1 .
F3 F 0.2203(7) 0.5766(2) 0.8605(5) 0.0404(11) Uiso 0.45 1 d A 1 .
F4 F 0.5333(8) 0.5879(3) 0.8400(5) 0.0636(16) Uiso 0.45 1 d A 1 .
F1A F 0.3202(6) 0.6714(2) 0.8636(4) 0.0291(11) Uiso 0.47 1 d A 2 .
F2A F 0.2695(7) 0.61727(19) 0.6946(4) 0.0421(13) Uiso 0.47 1 d A 2 .
F3A F 0.2921(8) 0.5647(2) 0.8730(4) 0.0466(12) Uiso 0.47 1 d A 2 .
F4A F 0.5507(6) 0.6002(2) 0.7961(5) 0.0536(13) Uiso 0.47 1 d A 2 .
F1B F 0.195(3) 0.5797(17) 0.796(4) 0.104(13) Uiso 0.08 1 d A 3 .
F2B F 0.438(4) 0.6112(10) 0.6938(14) 0.040(5) Uiso 0.08 1 d A 3 .
F3B F 0.369(4) 0.6624(10) 0.8961(19) 0.036 Uiso 0.08 1 d A 3 .
F4B F 0.427(4) 0.5602(10) 0.880(2) 0.063(7) Uiso 0.08 1 d A 3 .


_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 C10 1.373(3) . ?
O1 C14 1.441(3) . ?
O2 C11 1.372(3) . ?
O2 C15 1.445(3) . ?
N1 C1 1.349(3) . ?
N1 C5 1.348(3) . ?
N1 C16 1.492(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.375(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.415(4) . ?
C3 C4 1.396(4) . ?
C3 C6 1.459(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.371(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.332(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.467(4) . ?
C8 C9 1.407(4) . ?
C8 C13 1.397(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(4) . ?
C10 C11 1.414(4) . ?
C11 C12 1.382(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(4) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.498(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
B1 F1 1.425(5) . ?
B1 F2 1.359(5) . ?
B1 F3 1.437(6) . ?
B1 F4 1.385(7) . ?
B1 F1A 1.407(5) . ?
B1 F2A 1.448(6) . ?
B1 F3A 1.354(5) . ?
B1 F4A 1.410(6) . ?
B1 F1B 1.427(15) . ?
B1 F2B 1.423(14) . ?
B1 F3B 1.425(14) . ?
B1 F4B 1.428(14) . ?

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
C10 O1 C14 116.3(2) . . ?
C11 O2 C15 116.1(2) . . ?
C1 N1 C16 120.2(2) . . ?
C5 N1 C1 120.1(2) . . ?
C5 N1 C16 119.7(2) . . ?
N1 C1 H1 119.2 . . ?
N1 C1 C2 121.5(2) . . ?
C2 C1 H1 119.2 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.5(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C6 123.8(2) . . ?
C4 C3 C2 116.9(2) . . ?
C4 C3 C6 119.3(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
N1 C5 C4 120.7(3) . . ?
N1 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C3 C6 H6 116.7 . . ?
C7 C6 C3 126.5(3) . . ?
C7 C6 H6 116.7 . . ?
C6 C7 H7 117.1 . . ?
C6 C7 C8 125.7(2) . . ?
C8 C7 H7 117.1 . . ?
C9 C8 C7 119.5(2) . . ?
C13 C8 C7 122.2(2) . . ?
C13 C8 C9 118.3(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 H9 119.5 . . ?
O1 C10 C9 124.8(2) . . ?
O1 C10 C11 115.9(2) . . ?
C9 C10 C11 119.3(2) . . ?
O2 C11 C10 115.4(2) . . ?
O2 C11 C12 124.9(2) . . ?
C12 C11 C10 119.7(2) . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 121.1(3) . . ?
C12 C13 H13 119.5 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.4 . . ?
N1 C16 H16B 109.4 . . ?
N1 C16 C17 111.0(2) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
F1 B1 F3 111.9(3) . . ?
F1 B1 F2A 108.7(3) . . ?
F2 B1 F1 109.5(3) . . ?
F2 B1 F3 111.4(4) . . ?
F2 B1 F4 111.2(4) . . ?
F4 B1 F1 100.8(4) . . ?
F4 B1 F3 111.6(4) . . ?
F1A B1 F2A 103.0(3) . . ?
F1A B1 F4A 116.3(4) . . ?
F3A B1 F1A 108.1(4) . . ?
F3A B1 F2A 109.6(4) . . ?
F3A B1 F4A 108.3(4) . . ?
F4A B1 F2A 111.3(4) . . ?
F4A B1 F1B 138.4(17) . . ?
F4A B1 F2B 60.1(11) . . ?
F4A B1 F3B 101.7(13) . . ?
F2B B1 F1B 104(2) . . ?
F2B B1 F3B 130.2(15) . . ?
F2B B1 F4B 111.5(15) . . ?
F3B B1 F1B 115(2) . . ?
F3B B1 F4B 99.8(15) . . ?


_database_code_depnum_ccdc_archive 'CCDC 859813'
#######################################################################
#
#                 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_ff
_audit_creation_date             2014-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'F6 P, C17 H20 N O2'
_chemical_formula_sum            'C17 H21 F6 N O2 P'
_chemical_formula_weight         416.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.106(2)
_cell_length_b                   22.507(7)
_cell_length_c                   11.576(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.143(8)
_cell_angle_gamma                90.00
_cell_volume                     1851.5(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    827
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      29.737
_cell_measurement_theta_min      3.006
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.9700
_exptl_absorpt_correction_T_min  0.8800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_av_unetI/netI     0.1107
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14757
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         0.90
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2572
_reflns_number_total             4884
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         4884
_refine_ls_number_restraints     525
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_gt           0.0632
_refine_ls_restrained_S_all      1.168
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0519P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1431
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 P1-F1 \\sim P1-F2 \\sim P1-F3 \\sim P1-F4 \\sim P1-F5 \\sim P1-F6 \\sim P2-F2'
\\sim P2-F3' \\sim P2-F4' \\sim P2-
 F5' \\sim P2-F6'
 with sigma of 0.02
 F1-F3 \\sim F1-F4 \\sim F1-F5 \\sim F1-F6 \\sim F2-F3 \\sim F2-F4 \\sim F2-F5
\\sim F2-F6 \\sim F3-F4 \\sim F3-F6
 \\sim F4-F5 \\sim F5-F6 \\sim F1-F3' \\sim F1-F4' \\sim F1-F5' \\sim F1-F6'
\\sim F2'-F3' \\sim F2'-F4' \\sim F2'-
 F5' \\sim F2'-F6' \\sim F3'-F4' \\sim F3'-F6' \\sim F4'-F5' \\sim F5'-F6'
 with sigma of 0.02
 N1-C1 \\sim N1-C5 \\sim N1'-C1' \\sim N1'-C5
 with sigma of 0.02
 C1-C2 \\sim C4-C5 \\sim C1'-C2' \\sim C4'-C5
 with sigma of 0.02
 C2-C3 \\sim C3-C4 \\sim C2'-C3' \\sim C3'-C4'
 with sigma of 0.02
 C8-C9 \\sim C8'-C9'
 with sigma of 0.02
 C8-C13 \\sim C8'-C13'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(F2') \\sim Ueq, Uanis(F3') \\sim Ueq, Uanis(F4') \\sim Ueq, Uanis(F5')
\\sim Ueq, Uanis(F6') \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C1) \\sim Ueq,
Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim
Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(N1') \\sim Ueq, Uanis(C1') \\sim Ueq,
Uanis(C2') \\sim Ueq, Uanis(C3') \\sim Ueq, Uanis(C4') \\sim Ueq, Uanis(C6')
\\sim Ueq, Uanis(C7') \\sim Ueq, Uanis(C8') \\sim Ueq, Uanis(C9') \\sim Ueq,
Uanis(C13') \\sim Ueq, Uanis(C16') \\sim Ueq, Uanis(C17') \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(P2)=Sof(F2')=Sof(F3')=Sof(F4')=Sof(F5')=Sof(F6')=1-FVAR(1)
 Sof(P1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
 Sof(N1')=Sof(C1')=Sof(H1')=Sof(C2')=Sof(H2')=Sof(C3')=Sof(C4')=Sof(H4')=
 Sof(C6')=Sof(H6')=Sof(C7')=Sof(H7')=Sof(C8')=Sof(C9')=Sof(H9')=Sof(C13')=
 Sof(H13')=Sof(C16')=Sof(H16C)=Sof(H16D)=Sof(C17')=Sof(H17D)=Sof(H17E)=
 Sof(H17F)=Sof(H5B)=Sof(H10A)=1-FVAR(2)
 Sof(N1)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(C4)=Sof(H4)=Sof(C6)=
 Sof(H6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(C9)=Sof(H9)=Sof(C13)=Sof(H13)=Sof(C16)=
 Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(H5A)=Sof(H10)=
 FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C16'(H16C,H16D)
5.b Me refined with riding coordinates:
 C17(H17A,H17B,H17C), C17'(H17D,H17E,H17F), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C6(H6), C7(H7), C9(H9), C13(H13), C1'(H1'), C2'(H2'),
 C4'(H4'), C6'(H6'), C7'(H7'), C9'(H9'), C13'(H13'), C5(H5A), C5(H5B), C10(H10),
  C10(H10A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
F1 F 0.8667(5) 0.53933(11) -0.2625(2) 0.0661(9) Uani 1 1 d . . . .
P1 P 0.8379(5) 0.6053(2) -0.3152(3) 0.0357(7) Uani 0.773(8) 1 d A 1 . .
F2 F 0.8097(11) 0.6721(3) -0.3632(5) 0.081(2) Uani 0.773(8) 1 d A 1 . .
F3 F 0.6752(9) 0.6158(2) -0.2230(4) 0.0812(19) Uani 0.773(8) 1 d A 1 . .
F4 F 0.6898(8) 0.5833(3) -0.4072(4) 0.084(2) Uani 0.773(8) 1 d A 1 . .
F5 F 1.0027(6) 0.5970(2) -0.4070(4) 0.0752(16) Uani 0.773(8) 1 d A 1 . .
F6 F 0.9836(8) 0.63011(17) -0.2245(4) 0.0673(16) Uani 0.773(8) 1 d A 1 . .
P2 P 0.847(2) 0.5951(8) -0.3233(12) 0.063(6) Uani 0.227(8) 1 d A 2 . .
F2' F 0.835(3) 0.6546(6) -0.3967(12) 0.073(7) Uani 0.227(8) 1 d A 2 . U
F3' F 0.798(3) 0.6311(5) -0.2101(9) 0.070(6) Uani 0.227(8) 1 d A 2 . U
F4' F 0.6283(17) 0.5834(6) -0.3455(16) 0.072(6) Uani 0.227(8) 1 d A 2 . U
F5' F 0.895(3) 0.5596(6) -0.4405(8) 0.078(7) Uani 0.227(8) 1 d A 2 . U
F6' F 1.0679(19) 0.6079(8) -0.3041(18) 0.112(8) Uani 0.227(8) 1 d A 2 . U
O1 O 0.3603(5) 0.74048(12) 0.2175(3) 0.0541(9) Uani 1 1 d . . . .
O2 O 0.3471(5) 0.64176(12) 0.3352(2) 0.0490(8) Uani 1 1 d B . . .
N1 N 0.1386(16) 0.3350(5) -0.2613(8) 0.038(3) Uani 0.612(11) 1 d B 1 . U
C1 C 0.153(2) 0.3836(5) -0.3275(11) 0.046(3) Uani 0.612(11) 1 d B 1 . U
H1 H 0.1366 0.3800 -0.4087 0.055 Uiso 0.612(11) 1 calc B 1 R .
C2 C 0.1897(18) 0.4394(5) -0.2806(8) 0.031(2) Uani 0.612(11) 1 d B 1 . U
H2 H 0.2028 0.4727 -0.3303 0.038 Uiso 0.612(11) 1 calc B 1 R .
C3 C 0.2082(13) 0.4471(4) -0.1602(8) 0.0246(18) Uani 0.612(11) 1 d B 1 . U
C4 C 0.1968(19) 0.3933(4) -0.0948(7) 0.026(2) Uani 0.612(11) 1 d B 1 . U
H4 H 0.2029 0.3954 -0.0129 0.031 Uiso 0.612(11) 1 calc B 1 R .
C6 C 0.2384(9) 0.5052(3) -0.1133(6) 0.0272(19) Uani 0.612(11) 1 d B 1 . U
H6 H 0.2391 0.5377 -0.1656 0.033 Uiso 0.612(11) 1 calc B 1 R .
C7 C 0.2660(11) 0.5172(4) 0.0004(7) 0.0307(19) Uani 0.612(11) 1 d B 1 . U
H7 H 0.2677 0.4845 0.0523 0.037 Uiso 0.612(11) 1 calc B 1 R .
C8 C 0.2934(17) 0.5769(5) 0.0496(9) 0.024(2) Uani 0.612(11) 1 d B 1 . U
C9 C 0.301(2) 0.6270(5) -0.0177(11) 0.036(3) Uani 0.612(11) 1 d B 1 . U
H9 H 0.2918 0.6231 -0.0993 0.043 Uiso 0.612(11) 1 calc B 1 R .
C13 C 0.313(2) 0.5813(8) 0.1705(10) 0.028(3) Uani 0.612(11) 1 d B 1 . U
H13 H 0.3145 0.5468 0.2177 0.034 Uiso 0.612(11) 1 calc B 1 R .
C16 C 0.0944(18) 0.2780(4) -0.3211(11) 0.056(3) Uani 0.612(11) 1 d B 1 . U
H16A H 0.0557 0.2477 -0.2640 0.067 Uiso 0.612(11) 1 calc B 1 R .
H16B H -0.0103 0.2839 -0.3765 0.067 Uiso 0.612(11) 1 calc B 1 R .
C17 C 0.2647(15) 0.2580(5) -0.3830(8) 0.062(3) Uani 0.612(11) 1 d B 1 . U
H17A H 0.2376 0.2208 -0.4236 0.092 Uiso 0.612(11) 1 calc B 1 R .
H17B H 0.3670 0.2516 -0.3274 0.092 Uiso 0.612(11) 1 calc B 1 R .
H17C H 0.3024 0.2884 -0.4389 0.092 Uiso 0.612(11) 1 calc B 1 R .
N1' N 0.206(2) 0.3401(8) -0.2655(12) 0.041(5) Uani 0.388(11) 1 d B 2 . U
C1' C 0.197(3) 0.3964(8) -0.3115(16) 0.047(6) Uani 0.388(11) 1 d B 2 . U
H1' H 0.1885 0.4027 -0.3925 0.056 Uiso 0.388(11) 1 calc B 2 R .
C2' C 0.202(3) 0.4439(8) -0.2342(16) 0.040(4) Uani 0.388(11) 1 d B 2 . U
H2' H 0.1990 0.4834 -0.2631 0.047 Uiso 0.388(11) 1 calc B 2 R .
C3' C 0.211(2) 0.4345(6) -0.1159(13) 0.029(3) Uani 0.388(11) 1 d B 2 . U
C4' C 0.209(3) 0.3786(7) -0.0700(13) 0.038(5) Uani 0.388(11) 1 d B 2 . U
H4' H 0.2290 0.3705 0.0097 0.045 Uiso 0.388(11) 1 calc B 2 R .
C6' C 0.2366(18) 0.4852(6) -0.0289(11) 0.042(4) Uani 0.388(11) 1 d B 2 . U
H6' H 0.2402 0.4754 0.0509 0.050 Uiso 0.388(11) 1 calc B 2 R .
C7' C 0.2541(17) 0.5407(7) -0.0575(12) 0.041(4) Uani 0.388(11) 1 d B 2 . U
H7' H 0.2456 0.5491 -0.1378 0.049 Uiso 0.388(11) 1 calc B 2 R .
C8' C 0.285(4) 0.5918(9) 0.0181(16) 0.042(6) Uani 0.388(11) 1 d B 2 . U
C9' C 0.298(5) 0.6474(8) -0.027(2) 0.047(6) Uani 0.388(11) 1 d B 2 . U
H9' H 0.2876 0.6533 -0.1080 0.056 Uiso 0.388(11) 1 calc B 2 R .
C13' C 0.293(4) 0.5864(13) 0.1395(15) 0.031(5) Uani 0.388(11) 1 d B 2 . U
H13' H 0.2738 0.5483 0.1725 0.037 Uiso 0.388(11) 1 calc B 2 R .
C16' C 0.209(3) 0.2827(7) -0.3378(16) 0.053(4) Uani 0.388(11) 1 d B 2 . U
H16C H 0.2942 0.2886 -0.4042 0.063 Uiso 0.388(11) 1 calc B 2 R .
H16D H 0.2618 0.2503 -0.2898 0.063 Uiso 0.388(11) 1 calc B 2 R .
C17' C 0.0199(16) 0.2635(5) -0.3825(11) 0.035(3) Uani 0.388(11) 1 d B 2 . U
H17D H 0.0339 0.2268 -0.4272 0.053 Uiso 0.388(11) 1 calc B 2 R .
H17E H -0.0323 0.2947 -0.4322 0.053 Uiso 0.388(11) 1 calc B 2 R .
H17F H -0.0651 0.2565 -0.3174 0.053 Uiso 0.388(11) 1 calc B 2 R .
C5 C 0.1767(8) 0.33694(19) -0.1477(3) 0.0475(12) Uani 1 1 d . . . .
H5A H 0.1899 0.3015 -0.1040 0.057 Uiso 0.612(11) 1 calc B 1 R .
H5B H 0.1278 0.3005 -0.1193 0.057 Uiso 0.388(11) 1 calc B 2 R .
C10 C 0.3220(8) 0.6881(2) 0.0347(4) 0.0492(12) Uani 1 1 d . . . .
H10 H 0.3254 0.7231 -0.0112 0.059 Uiso 0.612(11) 1 calc B 1 R .
H10A H 0.3332 0.7255 -0.0029 0.059 Uiso 0.388(11) 1 calc B 2 R .
C11 C 0.3363(7) 0.68982(17) 0.1538(3) 0.0372(9) Uani 1 1 d B . . .
C12 C 0.3303(7) 0.63616(16) 0.2172(3) 0.0351(9) Uani 1 1 d . . . .
C14 C 0.3552(10) 0.79599(18) 0.1536(5) 0.0746(18) Uani 1 1 d . . . .
H14A H 0.3742 0.8293 0.2070 0.112 Uiso 1 1 calc . . R .
H14B H 0.2328 0.8001 0.1153 0.112 Uiso 1 1 calc . . R .
H14C H 0.4553 0.7960 0.0955 0.112 Uiso 1 1 calc . . R .
C15 C 0.3344(9) 0.5884(2) 0.4036(4) 0.0610(13) Uani 1 1 d . . . .
H15A H 0.3486 0.5984 0.4855 0.091 Uiso 1 1 calc B . R .
H15B H 0.4344 0.5608 0.3808 0.091 Uiso 1 1 calc . . R .
H15C H 0.2116 0.5696 0.3909 0.091 Uiso 1 1 calc . . R .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 P1 1.618(5) . ?
F1 P2 1.446(18) . ?
P1 F2 1.616(6) . ?
P1 F3 1.593(6) . ?
P1 F4 1.575(5) . ?
P1 F5 1.595(5) . ?
P1 F6 1.575(5) . ?
P2 F2' 1.588(16) . ?
P2 F3' 1.579(13) . ?
P2 F4' 1.598(13) . ?
P2 F5' 1.612(13) . ?
P2 F6' 1.609(13) . ?
O1 C11 1.369(5) . ?
O1 C14 1.452(5) . ?
O2 C12 1.377(4) . ?
O2 C15 1.442(5) . ?
N1 C1 1.341(11) . ?
N1 C16 1.490(15) . ?
N1 C5 1.343(9) . ?
C1 H1 0.9500 . ?
C1 C2 1.393(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.410(8) . ?
C3 C4 1.430(9) . ?
C3 C6 1.433(11) . ?
C4 H4 0.9500 . ?
C4 C5 1.415(10) . ?
C6 H6 0.9500 . ?
C6 C7 1.357(10) . ?
C7 H7 0.9500 . ?
C7 C8 1.472(14) . ?
C8 C9 1.370(11) . ?
C8 C13 1.410(11) . ?
C9 H9 0.9500 . ?
C9 C10 1.512(13) . ?
C13 H13 0.9500 . ?
C13 C12 1.353(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.478(14) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N1' C1' 1.377(16) . ?
N1' C16' 1.54(2) . ?
N1' C5 1.381(14) . ?
C1' H1' 0.9500 . ?
C1' C2' 1.395(16) . ?
C2' H2' 0.9500 . ?
C2' C3' 1.387(13) . ?
C3' C4' 1.367(13) . ?
C3' C6' 1.53(2) . ?
C4' H4' 0.9500 . ?
C4' C5 1.319(13) . ?
C6' H6' 0.9500 . ?
C6' C7' 1.30(2) . ?
C7' H7' 0.9500 . ?
C7' C8' 1.46(2) . ?
C8' C9' 1.358(16) . ?
C8' C13' 1.412(16) . ?
C9' H9' 0.9500 . ?
C9' C10 1.17(2) . ?
C13' H13' 0.9500 . ?
C13' C12 1.46(3) . ?
C16' H16C 0.9900 . ?
C16' H16D 0.9900 . ?
C16' C17' 1.50(2) . ?
C17' H17D 0.9800 . ?
C17' H17E 0.9800 . ?
C17' H17F 0.9800 . ?
C5 H5A 0.9500 . ?
C5 H5B 0.9500 . ?
C10 H10 0.9500 . ?
C10 H10A 0.9500 . ?
C10 C11 1.383(5) . ?
C11 C12 1.414(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
F2 P1 F1 177.9(4) . . ?
F3 P1 F1 88.5(3) . . ?
F3 P1 F2 90.2(4) . . ?
F3 P1 F5 178.1(4) . . ?
F4 P1 F1 92.9(3) . . ?
F4 P1 F2 88.8(3) . . ?
F4 P1 F3 90.8(3) . . ?
F4 P1 F5 90.2(3) . . ?
F5 P1 F1 93.0(3) . . ?
F5 P1 F2 88.3(3) . . ?
F6 P1 F1 89.5(3) . . ?
F6 P1 F2 88.9(3) . . ?
F6 P1 F3 88.7(3) . . ?
F6 P1 F4 177.6(4) . . ?
F6 P1 F5 90.2(3) . . ?
F1 P2 F2' 176.0(11) . . ?
F1 P2 F3' 93.6(9) . . ?
F1 P2 F4' 91.5(9) . . ?
F1 P2 F5' 87.6(8) . . ?
F1 P2 F6' 89.7(9) . . ?
F2' P2 F4' 90.2(10) . . ?
F2' P2 F5' 88.8(9) . . ?
F2' P2 F6' 88.5(10) . . ?
F3' P2 F2' 90.1(9) . . ?
F3' P2 F4' 90.1(9) . . ?
F3' P2 F5' 178.7(13) . . ?
F3' P2 F6' 90.7(9) . . ?
F4' P2 F5' 89.3(8) . . ?
F4' P2 F6' 178.5(14) . . ?
F6' P2 F5' 89.9(9) . . ?
C11 O1 C14 116.1(4) . . ?
C12 O2 C15 117.6(3) . . ?
C1 N1 C16 116.9(9) . . ?
C1 N1 C5 121.2(10) . . ?
C5 N1 C16 121.7(9) . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.8(12) . . ?
C2 C1 H1 119.1 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.9(11) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 114.5(9) . . ?
C2 C3 C6 120.0(9) . . ?
C4 C3 C6 125.5(8) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 C3 122.3(7) . . ?
C5 C4 H4 118.8 . . ?
C3 C6 H6 117.6 . . ?
C7 C6 C3 124.8(7) . . ?
C7 C6 H6 117.6 . . ?
C6 C7 H7 117.4 . . ?
C6 C7 C8 125.1(8) . . ?
C8 C7 H7 117.4 . . ?
C9 C8 C7 122.4(10) . . ?
C9 C8 C13 120.2(12) . . ?
C13 C8 C7 117.4(10) . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.6(10) . . ?
C10 C9 H9 119.2 . . ?
C8 C13 H13 121.0 . . ?
C12 C13 C8 118.0(12) . . ?
C12 C13 H13 121.0 . . ?
N1 C16 H16A 110.0 . . ?
N1 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?
C17 C16 N1 108.4(10) . . ?
C17 C16 H16A 110.0 . . ?
C17 C16 H16B 110.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1' N1' C16' 124.3(14) . . ?
C1' N1' C5 115.0(16) . . ?
C5 N1' C16' 119.8(14) . . ?
N1' C1' H1' 121.4 . . ?
N1' C1' C2' 117.2(16) . . ?
C2' C1' H1' 121.4 . . ?
C1' C2' H2' 119.4 . . ?
C3' C2' C1' 121.1(15) . . ?
C3' C2' H2' 119.4 . . ?
C2' C3' C6' 122.7(14) . . ?
C4' C3' C2' 121.7(14) . . ?
C4' C3' C6' 115.5(12) . . ?
C3' C4' H4' 123.5 . . ?
C3' C6' H6' 118.0 . . ?
C7' C6' C3' 124.0(13) . . ?
C7' C6' H6' 118.0 . . ?
C6' C7' H7' 115.9 . . ?
C6' C7' C8' 128.2(15) . . ?
C8' C7' H7' 115.9 . . ?
C9' C8' C7' 120.3(19) . . ?
C9' C8' C13' 117(2) . . ?
C13' C8' C7' 122.3(19) . . ?
C8' C9' H9' 120.1 . . ?
C8' C13' H13' 118.2 . . ?
C12 C13' H13' 118.2 . . ?
N1' C16' H16C 108.6 . . ?
N1' C16' H16D 108.6 . . ?
H16C C16' H16D 107.6 . . ?
C17' C16' N1' 114.5(15) . . ?
C17' C16' H16C 108.6 . . ?
C17' C16' H16D 108.6 . . ?
C16' C17' H17D 109.5 . . ?
C16' C17' H17E 109.5 . . ?
C16' C17' H17F 109.5 . . ?
H17D C17' H17E 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
N1 C5 C4 118.3(7) . . ?
N1 C5 H5A 120.9 . . ?
N1 C5 H5B 103.7 . . ?
C4 C5 H5A 120.9 . . ?
C9 C10 H10 122.2 . . ?
C11 C10 C9 115.6(6) . . ?
C11 C10 H10 122.2 . . ?
C11 C10 H10A 115.2 . . ?
O1 C11 C10 124.7(4) . . ?
O1 C11 C12 115.8(3) . . ?
C10 C11 C12 119.5(4) . . ?
O2 C12 C11 115.7(3) . . ?
C13 C12 O2 119.2(6) . . ?
C13 C12 C11 125.1(6) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_database_code_depnum_ccdc_archive 'CCDC 969549'
#######################################################################
#
#                 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_pi
_audit_creation_date             2014-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H20 N O2, C6 H2 N3 O7'
_chemical_formula_sum            'C23 H22 N4 O9'
_chemical_formula_weight         498.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   14.2243(10)
_cell_length_b                   14.4190(9)
_cell_length_c                   22.4404(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.933(4)
_cell_angle_gamma                90.00
_cell_volume                     4447.1(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.991
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9902
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14627
_diffrn_reflns_theta_full        53.37
_diffrn_reflns_theta_max         53.37
_diffrn_reflns_theta_min         3.22
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.886
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3462
_reflns_number_total             4653
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.823
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         4653
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1110
_refine_ls_R_factor_gt           0.0840
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1347P)²+9.3279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2049
_refine_ls_wR_factor_ref         0.2272
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C16'(H16C,H16D)
2.b Me refined with riding coordinates:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C14'(H14D,H14E,
 H14F), C15'(H15D,H15E,H15F), C17'(H17D,H17E,H17F)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13),
 C1'(H1'), C2'(H2'), C4'(H4'), C5'(H5'), C6'(H6'), C7'(H7'), C9'(H9'),
 C10'(H10'), C13'(H13'), C3P(H3P), C5P(H5P), C9P(H9P), C11P(H11P)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.3033(3) 0.9370(2) 0.18079(16) 0.0301(10) Uani 1 1 d . . .
O2 O 0.4440(2) 0.8325(2) 0.23783(15) 0.0284(9) Uani 1 1 d . . .
N1 N 0.7545(3) 1.0979(3) 0.62928(18) 0.0202(11) Uani 1 1 d . . .
C1 C 0.7638(4) 1.0107(4) 0.6114(2) 0.0234(14) Uani 1 1 d . . .
H1 H 0.8078 0.9699 0.6380 0.028 Uiso 1 1 calc . . R
C2 C 0.7113(4) 0.9798(4) 0.5557(3) 0.0275(14) Uani 1 1 d . . .
H2 H 0.7195 0.9177 0.5439 0.033 Uiso 1 1 calc . . R
C3 C 0.6453(4) 1.0375(4) 0.5151(2) 0.0206(13) Uani 1 1 d . . .
C4 C 0.6376(4) 1.1270(4) 0.5351(2) 0.0261(14) Uani 1 1 d . . .
H4 H 0.5937 1.1689 0.5094 0.031 Uiso 1 1 calc . . R
C5 C 0.6924(4) 1.1562(4) 0.5916(3) 0.0281(14) Uani 1 1 d . . .
H5 H 0.6866 1.2184 0.6043 0.034 Uiso 1 1 calc . . R
C6 C 0.5907(4) 1.0027(4) 0.4552(2) 0.0273(14) Uani 1 1 d . . .
H6 H 0.6030 0.9408 0.4448 0.033 Uiso 1 1 calc . . R
C7 C 0.5255(4) 1.0505(4) 0.4143(2) 0.0230(14) Uani 1 1 d . . .
H7 H 0.5135 1.1118 0.4260 0.028 Uiso 1 1 calc . . R
C8 C 0.4692(4) 1.0209(4) 0.3531(2) 0.0226(13) Uani 1 1 d . . .
C9 C 0.3955(4) 1.0778(4) 0.3204(2) 0.0261(14) Uani 1 1 d . . .
H9 H 0.3836 1.1352 0.3378 0.031 Uiso 1 1 calc . . R
C10 C 0.3388(4) 1.0529(4) 0.2626(2) 0.0273(14) Uani 1 1 d . . .
H10 H 0.2880 1.0927 0.2411 0.033 Uiso 1 1 calc . . R
C11 C 0.3561(4) 0.9701(4) 0.2362(2) 0.0230(13) Uani 1 1 d . . .
C12 C 0.4324(4) 0.9119(4) 0.2688(2) 0.0249(14) Uani 1 1 d . . .
C13 C 0.4869(4) 0.9365(4) 0.3263(2) 0.0239(14) Uani 1 1 d . . .
H13 H 0.5369 0.8964 0.3483 0.029 Uiso 1 1 calc . . R
C14 C 0.2210(5) 0.9921(4) 0.1496(3) 0.0507(19) Uani 1 1 d . . .
H14A H 0.1882 0.9623 0.1105 0.076 Uiso 1 1 calc . . R
H14B H 0.2431 1.0540 0.1414 0.076 Uiso 1 1 calc . . R
H14C H 0.1755 0.9975 0.1756 0.076 Uiso 1 1 calc . . R
C15 C 0.5317(4) 0.7810(4) 0.2619(2) 0.0343(15) Uani 1 1 d . . .
H15A H 0.5324 0.7264 0.2360 0.051 Uiso 1 1 calc . . R
H15B H 0.5347 0.7611 0.3041 0.051 Uiso 1 1 calc . . R
H15C H 0.5880 0.8203 0.2621 0.051 Uiso 1 1 calc . . R
C16 C 0.8182(4) 1.1280(4) 0.6902(2) 0.0333(15) Uani 1 1 d . . .
H16A H 0.8848 1.1383 0.6856 0.040 Uiso 1 1 calc . . R
H16B H 0.8218 1.0769 0.7202 0.040 Uiso 1 1 calc . . R
C17 C 0.7858(4) 1.2142(4) 0.7165(2) 0.0364(15) Uani 1 1 d . . .
H17A H 0.8309 1.2280 0.7565 0.055 Uiso 1 1 calc . . R
H17B H 0.7203 1.2047 0.7220 0.055 Uiso 1 1 calc . . R
H17C H 0.7848 1.2662 0.6882 0.055 Uiso 1 1 calc . . R
O3 O 0.8142(2) 0.6941(2) 0.17923(16) 0.0298(10) Uani 1 1 d . . .
O4 O 0.9365(2) 0.5789(2) 0.24239(14) 0.0251(9) Uani 1 1 d . . .
N2 N 1.2648(3) 0.8529(3) 0.62832(19) 0.0249(11) Uani 1 1 d . . .
C1' C 1.2682(4) 0.7624(4) 0.6133(2) 0.0246(14) Uani 1 1 d . . .
H1' H 1.3087 0.7209 0.6416 0.030 Uiso 1 1 calc . . R
C2' C 1.2143(4) 0.7302(4) 0.5582(3) 0.0261(14) Uani 1 1 d . . .
H2' H 1.2166 0.6661 0.5489 0.031 Uiso 1 1 calc . . R
C3' C 1.1549(4) 0.7894(4) 0.5143(2) 0.0229(14) Uani 1 1 d . . .
C4' C 1.1553(4) 0.8821(4) 0.5315(2) 0.0249(14) Uani 1 1 d . . .
H4' H 1.1168 0.9253 0.5036 0.030 Uiso 1 1 calc . . R
C5' C 1.2097(4) 0.9125(4) 0.5876(3) 0.0279(14) Uani 1 1 d . . .
H5' H 1.2086 0.9763 0.5979 0.033 Uiso 1 1 calc . . R
C6' C 1.0985(4) 0.7542(4) 0.4554(2) 0.0262(14) Uani 1 1 d . . .
H6' H 1.1092 0.6918 0.4455 0.031 Uiso 1 1 calc . . R
C7' C 1.0329(4) 0.8027(4) 0.4143(2) 0.0232(14) Uani 1 1 d . . .
H7' H 1.0231 0.8648 0.4255 0.028 Uiso 1 1 calc . . R
C8' C 0.9740(4) 0.7724(4) 0.3541(2) 0.0226(13) Uani 1 1 d . . .
C9' C 0.9058(4) 0.8329(4) 0.3199(2) 0.0254(14) Uani 1 1 d . . .
H9' H 0.8973 0.8918 0.3367 0.030 Uiso 1 1 calc . . R
C10' C 0.8492(4) 0.8100(4) 0.2613(3) 0.0269(14) Uani 1 1 d . . .
H10' H 0.8021 0.8523 0.2387 0.032 Uiso 1 1 calc . . R
C11' C 0.8626(4) 0.7251(4) 0.2367(2) 0.0230(13) Uani 1 1 d . . .
C12' C 0.9305(4) 0.6612(4) 0.2716(2) 0.0229(13) Uani 1 1 d . . .
C13' C 0.9851(4) 0.6844(4) 0.3291(2) 0.0231(13) Uani 1 1 d . . .
H13' H 1.0307 0.6413 0.3523 0.028 Uiso 1 1 calc . . R
C14' C 0.7536(4) 0.7610(4) 0.1403(3) 0.0361(15) Uani 1 1 d . . .
H14D H 0.7223 0.7324 0.1005 0.054 Uiso 1 1 calc . . R
H14E H 0.7933 0.8137 0.1338 0.054 Uiso 1 1 calc . . R
H14F H 0.7036 0.7827 0.1600 0.054 Uiso 1 1 calc . . R
C15' C 1.0214(4) 0.5247(4) 0.2669(2) 0.0295(14) Uani 1 1 d . . .
H15D H 1.0184 0.4678 0.2426 0.044 Uiso 1 1 calc . . R
H15E H 1.0251 0.5088 0.3099 0.044 Uiso 1 1 calc . . R
H15F H 1.0792 0.5604 0.2650 0.044 Uiso 1 1 calc . . R
C16' C 1.3253(4) 0.8843(4) 0.6894(2) 0.0318(15) Uani 1 1 d . . .
H16C H 1.3882 0.9076 0.6843 0.038 Uiso 1 1 calc . . R
H16D H 1.3393 0.8302 0.7175 0.038 Uiso 1 1 calc . . R
C17' C 1.2789(4) 0.9587(4) 0.7188(3) 0.0445(17) Uani 1 1 d . . .
H17D H 1.3224 0.9754 0.7589 0.067 Uiso 1 1 calc . . R
H17E H 1.2171 0.9360 0.7248 0.067 Uiso 1 1 calc . . R
H17F H 1.2670 1.0135 0.6921 0.067 Uiso 1 1 calc . . R
O1P O 0.8860(3) 0.5850(3) -0.01082(17) 0.0419(11) Uani 1 1 d . . .
O2P O 0.9734(3) 0.5567(3) 0.10838(17) 0.0365(10) Uani 1 1 d . . .
O3P O 1.0617(3) 0.6693(3) 0.15519(17) 0.0362(10) Uani 1 1 d . . .
O4P O 0.9971(3) 0.9817(3) 0.09106(18) 0.0346(10) Uani 1 1 d . . .
O5P O 0.8856(3) 1.0146(3) 0.00822(16) 0.0314(10) Uani 1 1 d . . .
O6P O 0.7273(3) 0.7813(3) -0.12570(18) 0.0401(11) Uani 1 1 d . . .
O7P O 0.7347(3) 0.6379(3) -0.10074(17) 0.0393(11) Uani 1 1 d . . .
N1P N 0.9974(3) 0.6389(4) 0.1125(2) 0.0271(11) Uani 1 1 d . . .
N2P N 0.9338(3) 0.9576(3) 0.0449(2) 0.0244(11) Uani 1 1 d . . .
N3P N 0.7622(3) 0.7189(3) -0.0901(2) 0.0258(11) Uani 1 1 d . . .
C1P C 0.8875(4) 0.6678(4) 0.0058(2) 0.0256(14) Uani 1 1 d . . .
C2P C 0.9467(4) 0.7032(4) 0.0646(2) 0.0246(14) Uani 1 1 d . . .
C3P C 0.9630(3) 0.7954(4) 0.0773(2) 0.0232(14) Uani 1 1 d . . .
H3P H 1.0057 0.8149 0.1152 0.028 Uiso 1 1 calc . . R
C4P C 0.9155(4) 0.8605(4) 0.0334(2) 0.0215(13) Uani 1 1 d . . .
C5P C 0.8503(3) 0.8326(4) -0.0203(2) 0.0224(14) Uani 1 1 d . . .
H5P H 0.8165 0.8778 -0.0486 0.027 Uiso 1 1 calc . . R
C6P C 0.8340(4) 0.7409(4) -0.0333(2) 0.0224(13) Uani 1 1 d . . .
O8P O 0.6216(3) 0.3298(3) 0.50499(16) 0.0380(10) Uani 1 1 d . . .
O9P O 0.7101(4) 0.3941(4) 0.6160(2) 0.0817(18) Uani 1 1 d . . .
O10P O 0.7893(3) 0.5185(3) 0.61589(17) 0.0381(11) Uani 1 1 d . . .
O11P O 0.6145(3) 0.7608(3) 0.48828(17) 0.0342(10) Uani 1 1 d . . .
O12P O 0.5094(3) 0.7275(3) 0.40273(18) 0.0352(10) Uani 1 1 d . . .
O13P O 0.4226(3) 0.4165(3) 0.34915(18) 0.0414(11) Uani 1 1 d . . .
O14P O 0.5137(3) 0.3024(3) 0.39091(17) 0.0411(11) Uani 1 1 d . . .
N4P N 0.7268(3) 0.4651(3) 0.5896(2) 0.0293(12) Uani 1 1 d . . .
N5P N 0.5692(3) 0.7039(3) 0.4500(2) 0.0247(11) Uani 1 1 d . . .
N6P N 0.4929(3) 0.3850(4) 0.3881(2) 0.0290(12) Uani 1 1 d . . .
C7P C 0.6130(4) 0.4128(4) 0.4905(2) 0.0226(13) Uani 1 1 d . . .
C8P C 0.6635(4) 0.4870(4) 0.5302(2) 0.0212(13) Uani 1 1 d . . .
C9P C 0.6513(3) 0.5789(4) 0.5164(2) 0.0222(14) Uani 1 1 d . . .
H9P H 0.6863 0.6238 0.5444 0.027 Uiso 1 1 calc . . R
C10P C 0.5882(4) 0.6070(4) 0.4616(2) 0.0218(13) Uani 1 1 d . . .
C11P C 0.5388(3) 0.5413(4) 0.4199(2) 0.0203(13) Uani 1 1 d . . .
H11P H 0.4962 0.5607 0.3820 0.024 Uiso 1 1 calc . . R
C12P C 0.5510(4) 0.4489(4) 0.4330(2) 0.0224(14) 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
O1 C11 1.362(6) . ?
O1 C14 1.440(6) . ?
O2 C12 1.371(6) . ?
O2 C15 1.432(6) . ?
N1 C1 1.337(7) . ?
N1 C5 1.348(7) . ?
N1 C16 1.497(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.355(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.400(7) . ?
C3 C4 1.379(7) . ?
C3 C6 1.458(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.319(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.463(7) . ?
C8 C9 1.385(7) . ?
C8 C13 1.408(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(7) . ?
C11 C12 1.416(7) . ?
C12 C13 1.371(7) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.498(8) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O3 C11' 1.371(6) . ?
O3 C14' 1.431(6) . ?
O4 C12' 1.370(6) . ?
O4 C15' 1.424(6) . ?
N2 C1' 1.352(7) . ?
N2 C5' 1.349(7) . ?
N2 C16' 1.489(7) . ?
C1' H1' 0.9500 . ?
C1' C2' 1.359(7) . ?
C2' H2' 0.9500 . ?
C2' C3' 1.407(7) . ?
C3' C4' 1.390(7) . ?
C3' C6' 1.450(7) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.369(7) . ?
C5' H5' 0.9500 . ?
C6' H6' 0.9500 . ?
C6' C7' 1.329(7) . ?
C7' H7' 0.9500 . ?
C7' C8' 1.461(7) . ?
C8' C9' 1.381(7) . ?
C8' C13' 1.414(7) . ?
C9' H9' 0.9500 . ?
C9' C10' 1.392(7) . ?
C10' H10' 0.9500 . ?
C10' C11' 1.377(7) . ?
C11' C12' 1.416(7) . ?
C12' C13' 1.365(7) . ?
C13' H13' 0.9500 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?
C15' H15D 0.9800 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9800 . ?
C16' H16C 0.9900 . ?
C16' H16D 0.9900 . ?
C16' C17' 1.500(8) . ?
C17' H17D 0.9800 . ?
C17' H17E 0.9800 . ?
C17' H17F 0.9800 . ?
O1P C1P 1.250(6) . ?
O2P N1P 1.230(5) . ?
O3P N1P 1.222(5) . ?
O4P N2P 1.233(5) . ?
O5P N2P 1.239(5) . ?
O6P N3P 1.221(6) . ?
O7P N3P 1.235(5) . ?
N1P C2P 1.463(7) . ?
N2P C4P 1.435(7) . ?
N3P C6P 1.448(7) . ?
C1P C2P 1.461(8) . ?
C1P C6P 1.455(8) . ?
C2P C3P 1.367(7) . ?
C3P H3P 0.9500 . ?
C3P C4P 1.402(7) . ?
C4P C5P 1.379(7) . ?
C5P H5P 0.9500 . ?
C5P C6P 1.361(7) . ?
O8P C7P 1.238(6) . ?
O9P N4P 1.236(6) . ?
O10P N4P 1.209(5) . ?
O11P N5P 1.241(5) . ?
O12P N5P 1.225(5) . ?
O13P N6P 1.233(5) . ?
O14P N6P 1.225(6) . ?
N4P C8P 1.438(7) . ?
N5P C10P 1.434(7) . ?
N6P C12P 1.456(7) . ?
C7P C8P 1.457(7) . ?
C7P C12P 1.458(7) . ?
C8P C9P 1.361(7) . ?
C9P H9P 0.9500 . ?
C9P C10P 1.382(7) . ?
C10P C11P 1.389(7) . ?
C11P H11P 0.9500 . ?
C11P C12P 1.365(7) . ?

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
C11 O1 C14 116.0(4) . . ?
C12 O2 C15 116.6(4) . . ?
C1 N1 C5 119.9(4) . . ?
C1 N1 C16 117.6(4) . . ?
C5 N1 C16 122.5(5) . . ?
N1 C1 H1 119.6 . . ?
N1 C1 C2 120.8(5) . . ?
C2 C1 H1 119.6 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.5(5) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C6 120.2(5) . . ?
C4 C3 C2 116.1(5) . . ?
C4 C3 C6 123.6(5) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.9(5) . . ?
C5 C4 H4 119.6 . . ?
N1 C5 C4 120.8(5) . . ?
N1 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C3 C6 H6 117.5 . . ?
C7 C6 C3 125.0(5) . . ?
C7 C6 H6 117.5 . . ?
C6 C7 H7 116.0 . . ?
C6 C7 C8 128.1(5) . . ?
C8 C7 H7 116.0 . . ?
C9 C8 C7 118.8(5) . . ?
C9 C8 C13 118.6(5) . . ?
C13 C8 C7 122.6(5) . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.4(5) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.9(5) . . ?
C11 C10 H10 120.0 . . ?
O1 C11 C10 125.1(5) . . ?
O1 C11 C12 115.6(5) . . ?
C10 C11 C12 119.2(5) . . ?
O2 C12 C11 114.2(5) . . ?
C13 C12 O2 125.5(5) . . ?
C13 C12 C11 120.3(5) . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.4(5) . . ?
C12 C13 H13 119.8 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 108.5 . . ?
N1 C16 H16B 108.5 . . ?
N1 C16 C17 115.1(4) . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11' O3 C14' 115.6(4) . . ?
C12' O4 C15' 116.2(4) . . ?
C1' N2 C16' 118.2(4) . . ?
C5' N2 C1' 119.9(5) . . ?
C5' N2 C16' 121.8(5) . . ?
N2 C1' H1' 119.8 . . ?
N2 C1' C2' 120.5(5) . . ?
C2' C1' H1' 119.8 . . ?
C1' C2' H2' 119.1 . . ?
C1' C2' C3' 121.8(5) . . ?
C3' C2' H2' 119.1 . . ?
C2' C3' C6' 121.1(5) . . ?
C4' C3' C2' 115.5(5) . . ?
C4' C3' C6' 123.4(5) . . ?
C3' C4' H4' 119.2 . . ?
C5' C4' C3' 121.6(5) . . ?
C5' C4' H4' 119.2 . . ?
N2 C5' C4' 120.7(5) . . ?
N2 C5' H5' 119.7 . . ?
C4' C5' H5' 119.7 . . ?
C3' C6' H6' 117.5 . . ?
C7' C6' C3' 125.0(5) . . ?
C7' C6' H6' 117.5 . . ?
C6' C7' H7' 115.9 . . ?
C6' C7' C8' 128.1(5) . . ?
C8' C7' H7' 115.9 . . ?
C9' C8' C7' 118.6(5) . . ?
C9' C8' C13' 118.7(5) . . ?
C13' C8' C7' 122.6(5) . . ?
C8' C9' H9' 119.1 . . ?
C8' C9' C10' 121.9(5) . . ?
C10' C9' H9' 119.1 . . ?
C9' C10' H10' 120.5 . . ?
C11' C10' C9' 118.9(5) . . ?
C11' C10' H10' 120.5 . . ?
O3 C11' C10' 125.4(5) . . ?
O3 C11' C12' 114.5(5) . . ?
C10' C11' C12' 120.1(5) . . ?
O4 C12' C11' 114.6(5) . . ?
C13' C12' O4 125.0(5) . . ?
C13' C12' C11' 120.4(5) . . ?
C8' C13' H13' 120.0 . . ?
C12' C13' C8' 120.0(5) . . ?
C12' C13' H13' 120.0 . . ?
O3 C14' H14D 109.5 . . ?
O3 C14' H14E 109.5 . . ?
O3 C14' H14F 109.5 . . ?
H14D C14' H14E 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
O4 C15' H15D 109.5 . . ?
O4 C15' H15E 109.5 . . ?
O4 C15' H15F 109.5 . . ?
H15D C15' H15E 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
N2 C16' H16C 108.7 . . ?
N2 C16' H16D 108.7 . . ?
N2 C16' C17' 114.0(4) . . ?
H16C C16' H16D 107.6 . . ?
C17' C16' H16C 108.7 . . ?
C17' C16' H16D 108.7 . . ?
C16' C17' H17D 109.5 . . ?
C16' C17' H17E 109.5 . . ?
C16' C17' H17F 109.5 . . ?
H17D C17' H17E 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
O2P N1P C2P 118.7(5) . . ?
O3P N1P O2P 122.8(5) . . ?
O3P N1P C2P 118.4(5) . . ?
O4P N2P O5P 122.0(4) . . ?
O4P N2P C4P 119.0(5) . . ?
O5P N2P C4P 118.9(4) . . ?
O6P N3P O7P 121.0(4) . . ?
O6P N3P C6P 119.4(5) . . ?
O7P N3P C6P 119.6(5) . . ?
O1P C1P C2P 124.4(5) . . ?
O1P C1P C6P 123.0(5) . . ?
C6P C1P C2P 112.5(5) . . ?
C1P C2P N1P 120.2(5) . . ?
C3P C2P N1P 115.9(5) . . ?
C3P C2P C1P 123.8(5) . . ?
C2P C3P H3P 120.7 . . ?
C2P C3P C4P 118.6(5) . . ?
C4P C3P H3P 120.7 . . ?
C3P C4P N2P 119.6(5) . . ?
C5P C4P N2P 119.5(5) . . ?
C5P C4P C3P 120.9(5) . . ?
C4P C5P H5P 119.7 . . ?
C6P C5P C4P 120.6(5) . . ?
C6P C5P H5P 119.7 . . ?
N3P C6P C1P 120.9(5) . . ?
C5P C6P N3P 116.3(5) . . ?
C5P C6P C1P 122.7(5) . . ?
O9P N4P C8P 118.3(5) . . ?
O10P N4P O9P 120.2(5) . . ?
O10P N4P C8P 121.2(5) . . ?
O11P N5P C10P 118.6(4) . . ?
O12P N5P O11P 122.4(4) . . ?
O12P N5P C10P 119.0(5) . . ?
O13P N6P C12P 118.0(5) . . ?
O14P N6P O13P 122.4(5) . . ?
O14P N6P C12P 119.6(5) . . ?
O8P C7P C8P 123.3(5) . . ?
O8P C7P C12P 125.0(5) . . ?
C8P C7P C12P 111.7(5) . . ?
N4P C8P C7P 119.8(5) . . ?
C9P C8P N4P 116.0(5) . . ?
C9P C8P C7P 124.1(5) . . ?
C8P C9P H9P 119.9 . . ?
C8P C9P C10P 120.2(5) . . ?
C10P C9P H9P 119.9 . . ?
C9P C10P N5P 119.7(5) . . ?
C9P C10P C11P 119.9(5) . . ?
C11P C10P N5P 120.2(5) . . ?
C10P C11P H11P 119.8 . . ?
C12P C11P C10P 120.4(5) . . ?
C12P C11P H11P 119.8 . . ?
N6P C12P C7P 119.5(5) . . ?
C11P C12P N6P 116.8(5) . . ?
C11P C12P C7P 123.6(5) . . ?

_database_code_depnum_ccdc_archive 'CCDC 969551'
#######################################################################
#
#                 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_p21c
_audit_creation_date             2014-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 H2 N3 O7, C17 H20 N O2, C3 H3'
_chemical_formula_sum            'C26 H25 N4 O9'
_chemical_formula_weight         537.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.7370(10)
_cell_length_b                   26.623(2)
_cell_length_c                   8.2528(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.714(3)
_cell_angle_gamma                90.00
_cell_volume                     2427.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9989
_exptl_absorpt_correction_T_min  0.9789
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1896
_diffrn_reflns_av_unetI/netI     0.1654
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            22602
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         1.84
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2350
_reflns_number_total             5023
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       0.254(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         5023
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1808
_refine_ls_R_factor_gt           0.0808
_refine_ls_restrained_S_all      0.914
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1157P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1869
_refine_ls_wR_factor_ref         0.2235
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C5A(H5A), C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9),
 C12(H12), C13(H13), C1S(H1S), C2S(H2S), C3S(H3S)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1A O 0.4355(3) 0.26978(10) -0.1011(4) 0.0436(8) Uani 1 1 d . . .
O2A O 0.4093(3) 0.36797(11) -0.1246(4) 0.0483(8) Uani 1 1 d . . .
O3A O 0.5564(3) 0.41366(10) 0.0289(4) 0.0519(9) Uani 1 1 d . . .
O4A O 0.8528(3) 0.35405(12) 0.5326(4) 0.0515(9) Uani 1 1 d . . .
O5A O 0.8758(3) 0.27430(11) 0.5817(4) 0.0542(9) Uani 1 1 d . . .
O6A O 0.6308(3) 0.15677(12) 0.1969(6) 0.0878(15) Uani 1 1 d . . .
O7A O 0.4592(3) 0.17629(12) 0.0231(5) 0.0725(12) Uani 1 1 d . . .
N1A N 0.5066(3) 0.37272(13) -0.0076(4) 0.0385(8) Uani 1 1 d . . .
N2A N 0.8231(3) 0.31014(14) 0.4946(5) 0.0423(9) Uani 1 1 d . . .
N3A N 0.5591(3) 0.18790(12) 0.1205(5) 0.0395(9) Uani 1 1 d . . .
C1A C 0.5199(4) 0.27879(14) 0.0350(5) 0.0342(9) Uani 1 1 d . . .
C2A C 0.5643(4) 0.32919(14) 0.0916(5) 0.0343(9) Uani 1 1 d . . .
C3A C 0.6621(4) 0.33952(15) 0.2378(5) 0.0379(10) Uani 1 1 d . . .
H3A H 0.6873 0.3732 0.2679 0.045 Uiso 1 1 calc . . R
C4A C 0.7227(4) 0.29982(15) 0.3397(5) 0.0374(10) Uani 1 1 d . . .
C5A C 0.6876(4) 0.25096(15) 0.2967(5) 0.0356(10) Uani 1 1 d . . .
H5A H 0.7310 0.2243 0.3670 0.043 Uiso 1 1 calc . . R
C6A C 0.5899(4) 0.24060(14) 0.1522(5) 0.0346(9) Uani 1 1 d . . .
O1 O 0.9078(3) 0.07016(10) 0.5672(4) 0.0436(8) Uani 1 1 d . . .
O2 O 1.0455(3) 0.00966(10) 0.7958(4) 0.0418(8) Uani 1 1 d . . .
N1 N 1.2129(3) 0.40245(11) 1.0474(4) 0.0335(8) Uani 1 1 d . . .
C1 C 1.2857(4) 0.37284(15) 1.1710(5) 0.0366(10) Uani 1 1 d . . .
H1 H 1.3419 0.3879 1.2703 0.044 Uiso 1 1 calc . . R
C2 C 1.2810(4) 0.32179(14) 1.1576(5) 0.0346(9) Uani 1 1 d . . .
H2 H 1.3349 0.3019 1.2462 0.042 Uiso 1 1 calc . . R
C3 C 1.1982(4) 0.29851(15) 1.0160(5) 0.0341(9) Uani 1 1 d . . .
C4 C 1.1240(4) 0.33015(15) 0.8865(5) 0.0369(10) Uani 1 1 d . . .
H4 H 1.0672 0.3160 0.7858 0.044 Uiso 1 1 calc . . R
C5 C 1.1335(4) 0.38106(15) 0.9052(5) 0.0379(10) Uani 1 1 d . . .
H5 H 1.0833 0.4020 0.8164 0.045 Uiso 1 1 calc . . R
C6 C 1.1914(4) 0.24388(15) 1.0106(5) 0.0357(10) Uani 1 1 d . . .
H6 H 1.2520 0.2255 1.0960 0.043 Uiso 1 1 calc . . R
C7 C 1.1045(4) 0.21796(15) 0.8918(5) 0.0365(10) Uani 1 1 d . . .
H7 H 1.0444 0.2370 0.8082 0.044 Uiso 1 1 calc . . R
C8 C 1.0933(4) 0.16340(15) 0.8786(5) 0.0359(10) Uani 1 1 d . . .
C9 C 1.0019(3) 0.14337(15) 0.7347(5) 0.0343(9) Uani 1 1 d . . .
H9 H 0.9480 0.1654 0.6540 0.041 Uiso 1 1 calc . . R
C10 C 0.9899(3) 0.09292(15) 0.7100(5) 0.0355(10) Uani 1 1 d . . .
C11 C 1.0663(4) 0.05935(14) 0.8290(5) 0.0361(10) Uani 1 1 d . . .
C12 C 1.1575(4) 0.07926(15) 0.9710(5) 0.0368(10) Uani 1 1 d . . .
H12 H 1.2113 0.0573 1.0519 0.044 Uiso 1 1 calc . . R
C13 C 1.1703(4) 0.13056(15) 0.9947(5) 0.0375(10) Uani 1 1 d . . .
H13 H 1.2328 0.1435 1.0920 0.045 Uiso 1 1 calc . . R
C14 C 0.8258(4) 0.10242(15) 0.4439(6) 0.0446(11) Uani 1 1 d . . .
H14A H 0.7680 0.0821 0.3545 0.067 Uiso 1 1 calc . . GR
H14B H 0.8712 0.1241 0.3915 0.067 Uiso 1 1 calc . . GR
H14C H 0.7819 0.1232 0.5013 0.067 Uiso 1 1 calc . . GR
C15 C 1.1241(4) -0.02477(16) 0.9158(6) 0.0490(12) Uani 1 1 d . . .
H15A H 1.0991 -0.0593 0.8798 0.074 Uiso 1 1 calc . . GR
H15B H 1.1195 -0.0189 1.0306 0.074 Uiso 1 1 calc . . GR
H15C H 1.2075 -0.0196 0.9189 0.074 Uiso 1 1 calc . . GR
C16 C 1.2212(4) 0.45801(14) 1.0604(6) 0.0409(10) Uani 1 1 d . . .
H16A H 1.2655 0.4676 1.1812 0.049 Uiso 1 1 calc . . R
H16B H 1.1387 0.4724 1.0277 0.049 Uiso 1 1 calc . . R
C17 C 1.2851(4) 0.47952(15) 0.9456(6) 0.0459(11) Uani 1 1 d . . .
H17A H 1.2362 0.4736 0.8250 0.069 Uiso 1 1 calc . . GR
H17B H 1.3641 0.4632 0.9710 0.069 Uiso 1 1 calc . . GR
H17C H 1.2965 0.5157 0.9662 0.069 Uiso 1 1 calc . . GR
C1S C 0.5379(4) 0.45299(17) 0.4678(6) 0.0474(12) Uani 1 1 d . . .
H1S H 0.5649 0.4209 0.4458 0.057 Uiso 1 1 calc . . R
C2S C 0.5004(4) 0.46012(17) 0.6083(6) 0.0441(11) Uani 1 1 d . . .
H2S H 0.4997 0.4328 0.6822 0.053 Uiso 1 1 calc . . R
C3S C 0.4641(4) 0.50719(18) 0.6397(6) 0.0497(12) Uani 1 1 d . . .
H3S H 0.4400 0.5123 0.7374 0.060 Uiso 1 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C1A 1.245(5) . ?
O2A N1A 1.228(4) . ?
O3A N1A 1.226(4) . ?
O4A N2A 1.230(4) . ?
O5A N2A 1.228(4) . ?
O6A N3A 1.198(4) . ?
O7A N3A 1.217(4) . ?
N1A C2A 1.448(5) . ?
N2A C4A 1.443(5) . ?
N3A C6A 1.450(5) . ?
C1A C2A 1.458(5) . ?
C1A C6A 1.452(5) . ?
C2A C3A 1.383(6) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.388(6) . ?
C4A C5A 1.374(6) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.376(5) . ?
O1 C10 1.385(4) . ?
O1 C14 1.428(5) . ?
O2 C11 1.356(5) . ?
O2 C15 1.434(5) . ?
N1 C1 1.343(5) . ?
N1 C5 1.353(5) . ?
N1 C16 1.484(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.363(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(5) . ?
C3 C4 1.408(6) . ?
C3 C6 1.457(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.364(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.343(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.459(5) . ?
C8 C9 1.410(5) . ?
C8 C13 1.384(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.359(5) . ?
C10 C11 1.405(5) . ?
C11 C12 1.398(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(6) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.505(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C1S H1S 0.9500 . ?
C1S C2S 1.385(6) . ?
C1S C3S 1.377(6) 3_666 ?
C2S H2S 0.9500 . ?
C2S C3S 1.376(6) . ?
C3S C1S 1.377(6) 3_666 ?
C3S H3S 0.9500 . ?

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
O2A N1A C2A 119.7(3) . . ?
O3A N1A O2A 121.7(3) . . ?
O3A N1A C2A 118.6(3) . . ?
O4A N2A C4A 118.9(3) . . ?
O5A N2A O4A 123.1(4) . . ?
O5A N2A C4A 118.0(3) . . ?
O6A N3A O7A 121.4(4) . . ?
O6A N3A C6A 119.1(4) . . ?
O7A N3A C6A 119.4(3) . . ?
O1A C1A C2A 123.8(4) . . ?
O1A C1A C6A 124.4(4) . . ?
C6A C1A C2A 111.7(3) . . ?
N1A C2A C1A 120.4(3) . . ?
C3A C2A N1A 115.2(3) . . ?
C3A C2A C1A 124.3(4) . . ?
C2A C3A H3A 120.6 . . ?
C2A C3A C4A 118.8(4) . . ?
C4A C3A H3A 120.6 . . ?
C3A C4A N2A 119.4(4) . . ?
C5A C4A N2A 119.5(4) . . ?
C5A C4A C3A 121.1(4) . . ?
C4A C5A H5A 119.9 . . ?
C4A C5A C6A 120.2(4) . . ?
C6A C5A H5A 119.9 . . ?
N3A C6A C1A 120.5(3) . . ?
C5A C6A N3A 115.7(3) . . ?
C5A C6A C1A 123.8(4) . . ?
C10 O1 C14 116.8(3) . . ?
C11 O2 C15 117.0(3) . . ?
C1 N1 C5 119.1(3) . . ?
C1 N1 C16 121.4(3) . . ?
C5 N1 C16 119.4(3) . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.7(4) . . ?
C2 C1 H1 119.1 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.7(4) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 116.7(4) . . ?
C2 C3 C6 119.1(4) . . ?
C4 C3 C6 124.1(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 121.5(4) . . ?
N1 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C3 C6 H6 118.1 . . ?
C7 C6 C3 123.8(4) . . ?
C7 C6 H6 118.1 . . ?
C6 C7 H7 116.8 . . ?
C6 C7 C8 126.4(4) . . ?
C8 C7 H7 116.8 . . ?
C9 C8 C7 117.6(3) . . ?
C13 C8 C7 123.8(4) . . ?
C13 C8 C9 118.6(4) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(4) . . ?
C10 C9 H9 119.6 . . ?
O1 C10 C11 114.4(3) . . ?
C9 C10 O1 124.6(3) . . ?
C9 C10 C11 121.0(4) . . ?
O2 C11 C10 116.8(3) . . ?
O2 C11 C12 125.0(4) . . ?
C12 C11 C10 118.2(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.8(4) . . ?
C12 C13 H13 119.6 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.3 . . ?
N1 C16 H16B 109.3 . . ?
N1 C16 C17 111.6(3) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2S C1S H1S 120.2 . . ?
C3S C1S H1S 120.2 3_666 . ?
C3S C1S C2S 119.5(4) 3_666 . ?
C1S C2S H2S 120.4 . . ?
C3S C2S C1S 119.2(4) . . ?
C3S C2S H2S 120.4 . . ?
C1S C3S H3S 119.4 3_666 . ?
C2S C3S C1S 121.3(4) . 3_666 ?
C2S C3S H3S 119.4 . . ?

_database_code_depnum_ccdc_archive 'CCDC 969550'
#######################################################################
#
#                 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_bb
_audit_creation_date             2014-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H20 N O2, C24 H20 B'
_chemical_formula_sum            'C41 H40 B N O2'
_chemical_formula_weight         589.55
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'

_cell_length_a                   8.9861(4)
_cell_length_b                   9.0343(4)
_cell_length_c                   40.1047(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3255.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_correction_T_min  0.9546
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0961
_diffrn_reflns_av_unetI/netI     0.1329
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            29245
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.03
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5608
_reflns_number_total             9470
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(17)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         9470
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0732
_refine_ls_restrained_S_all      0.962
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0448P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1282
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13),
 C2'(H2'), C3'(H3'), C4'(H4'), C5'(H5'), C6'(H6'), C8'(H8'), C9'(H9'),
 C10'(H10'), C11'(H11'), C12'(H12'), C14'(H14'), C15'(H15'), C16'(H16'),
 C17'(H17'), C18'(H18'), C20'(H20'), C21'(H21'), C22'(H22'), C23'(H23'),
 C24'(H24')
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.6885(2) 0.4933(2) 0.22219(4) 0.0286(5) Uani 1 1 d . . .
O2 O 0.9250(2) 0.6318(2) 0.20363(4) 0.0315(5) Uani 1 1 d . . .
N1 N 1.3532(2) 0.9747(3) 0.41553(5) 0.0214(5) Uani 1 1 d . . .
C1 C 1.2805(3) 0.8499(3) 0.42411(7) 0.0243(6) Uani 1 1 d . . .
H1 H 1.3007 0.8046 0.4450 0.029 Uiso 1 1 calc . . R
C2 C 1.1787(3) 0.7878(3) 0.40321(7) 0.0260(6) Uani 1 1 d . . .
H2 H 1.1262 0.7017 0.4101 0.031 Uiso 1 1 calc . . R
C3 C 1.1503(3) 0.8481(3) 0.37203(7) 0.0257(6) Uani 1 1 d . . .
C4 C 1.2279(3) 0.9781(3) 0.36361(7) 0.0275(6) Uani 1 1 d . . .
H4 H 1.2115 1.0240 0.3426 0.033 Uiso 1 1 calc . . R
C5 C 1.3277(3) 1.0389(3) 0.38578(6) 0.0235(6) Uani 1 1 d . . .
H5 H 1.3792 1.1271 0.3800 0.028 Uiso 1 1 calc . . R
C6 C 1.0437(3) 0.7721(3) 0.34992(7) 0.0288(7) Uani 1 1 d . . .
H6 H 0.9691 0.7118 0.3598 0.035 Uiso 1 1 calc . . R
C7 C 1.0468(3) 0.7838(3) 0.31737(7) 0.0300(7) Uani 1 1 d . . .
H7 H 1.1200 0.8473 0.3080 0.036 Uiso 1 1 calc . . R
C8 C 0.9457(3) 0.7062(3) 0.29383(7) 0.0280(7) Uani 1 1 d . . .
C9 C 0.8189(3) 0.6314(3) 0.30376(7) 0.0301(7) Uani 1 1 d . . .
H9 H 0.7928 0.6291 0.3267 0.036 Uiso 1 1 calc . . R
C10 C 0.7286(3) 0.5590(3) 0.28051(7) 0.0265(6) Uani 1 1 d . . .
H10 H 0.6412 0.5090 0.2876 0.032 Uiso 1 1 calc . . R
C11 C 0.7668(3) 0.5606(3) 0.24726(6) 0.0224(6) Uani 1 1 d . . .
C12 C 0.8962(3) 0.6364(3) 0.23718(6) 0.0237(6) Uani 1 1 d . . .
C13 C 0.9827(3) 0.7080(3) 0.26023(7) 0.0277(7) Uani 1 1 d . . .
H13 H 1.0692 0.7595 0.2531 0.033 Uiso 1 1 calc . . R
C14 C 0.5590(3) 0.4116(4) 0.23124(8) 0.0421(9) Uani 1 1 d . . .
H14A H 0.5118 0.3718 0.2111 0.063 Uiso 1 1 calc . . GR
H14B H 0.4889 0.4769 0.2428 0.063 Uiso 1 1 calc . . GR
H14C H 0.5871 0.3298 0.2460 0.063 Uiso 1 1 calc . . GR
C15 C 1.0554(4) 0.7041(5) 0.19184(8) 0.0536(11) Uani 1 1 d . . .
H15A H 1.0616 0.6938 0.1676 0.080 Uiso 1 1 calc . . GR
H15B H 1.1433 0.6591 0.2021 0.080 Uiso 1 1 calc . . GR
H15C H 1.0512 0.8094 0.1977 0.080 Uiso 1 1 calc . . GR
C16 C 1.4691(3) 1.0354(4) 0.43834(7) 0.0307(7) Uani 1 1 d . . .
H16A H 1.5140 1.1242 0.4280 0.037 Uiso 1 1 calc . . R
H16B H 1.5487 0.9607 0.4412 0.037 Uiso 1 1 calc . . R
C17 C 1.4082(3) 1.0762(4) 0.47205(6) 0.0340(7) Uani 1 1 d . . .
H17A H 1.3325 1.1535 0.4695 0.051 Uiso 1 1 calc . . GR
H17B H 1.4891 1.1131 0.4862 0.051 Uiso 1 1 calc . . GR
H17C H 1.3633 0.9887 0.4824 0.051 Uiso 1 1 calc . . GR
B1 B 0.6101(3) 0.5115(3) 0.40636(7) 0.0187(6) Uani 1 1 d . . .
C1' C 0.6728(3) 0.6814(3) 0.39791(6) 0.0185(5) Uani 1 1 d . . .
C2' C 0.6175(3) 0.7727(3) 0.37276(6) 0.0226(6) Uani 1 1 d . . .
H2' H 0.5415 0.7357 0.3585 0.027 Uiso 1 1 calc . . R
C3' C 0.6698(3) 0.9173(3) 0.36764(6) 0.0245(6) Uani 1 1 d . . .
H3' H 0.6316 0.9747 0.3497 0.029 Uiso 1 1 calc . . R
C4' C 0.7760(3) 0.9764(3) 0.38842(7) 0.0248(6) Uani 1 1 d . . .
H4' H 0.8089 1.0755 0.3855 0.030 Uiso 1 1 calc . . R
C5' C 0.8346(3) 0.8897(3) 0.41379(6) 0.0233(6) Uani 1 1 d . . .
H5' H 0.9080 0.9289 0.4283 0.028 Uiso 1 1 calc . . R
C6' C 0.7848(3) 0.7441(3) 0.41778(6) 0.0206(6) Uani 1 1 d . . .
H6' H 0.8288 0.6849 0.4347 0.025 Uiso 1 1 calc . . R
C7' C 0.7558(3) 0.4102(3) 0.41645(6) 0.0200(6) Uani 1 1 d . . .
C8' C 0.7650(3) 0.3222(3) 0.44501(6) 0.0209(6) Uani 1 1 d . . .
H8' H 0.6838 0.3218 0.4602 0.025 Uiso 1 1 calc . . R
C9' C 0.8885(3) 0.2352(3) 0.45211(6) 0.0267(6) Uani 1 1 d . . .
H9' H 0.8896 0.1764 0.4718 0.032 Uiso 1 1 calc . . R
C10' C 1.0097(3) 0.2331(3) 0.43095(7) 0.0282(7) Uani 1 1 d . . .
H10' H 1.0942 0.1739 0.4359 0.034 Uiso 1 1 calc . . R
C11' C 1.0056(3) 0.3193(3) 0.40221(7) 0.0269(6) Uani 1 1 d . . .
H11' H 1.0874 0.3191 0.3872 0.032 Uiso 1 1 calc . . R
C12' C 0.8808(3) 0.4062(3) 0.39556(6) 0.0223(6) Uani 1 1 d . . .
H12' H 0.8805 0.4653 0.3760 0.027 Uiso 1 1 calc . . R
C13' C 0.4960(3) 0.5299(3) 0.43823(6) 0.0200(6) Uani 1 1 d . . .
C14' C 0.5386(3) 0.6091(3) 0.46719(6) 0.0233(6) Uani 1 1 d . . .
H14' H 0.6372 0.6468 0.4684 0.028 Uiso 1 1 calc . . R
C15' C 0.4439(3) 0.6345(3) 0.49384(7) 0.0263(7) Uani 1 1 d . . .
H15' H 0.4784 0.6886 0.5126 0.032 Uiso 1 1 calc . . R
C16' C 0.2992(3) 0.5814(3) 0.49329(6) 0.0244(6) Uani 1 1 d . . .
H16' H 0.2327 0.6011 0.5112 0.029 Uiso 1 1 calc . . R
C17' C 0.2542(3) 0.4986(3) 0.46594(7) 0.0265(6) Uani 1 1 d . . .
H17' H 0.1563 0.4591 0.4652 0.032 Uiso 1 1 calc . . R
C18' C 0.3516(3) 0.4731(3) 0.43958(6) 0.0233(6) Uani 1 1 d . . .
H18' H 0.3180 0.4138 0.4215 0.028 Uiso 1 1 calc . . R
C19' C 0.5262(3) 0.4418(3) 0.37340(6) 0.0188(6) Uani 1 1 d . . .
C20' C 0.5844(3) 0.3248(3) 0.35414(6) 0.0211(6) Uani 1 1 d . . .
H20' H 0.6752 0.2801 0.3609 0.025 Uiso 1 1 calc . . R
C21' C 0.5136(3) 0.2719(3) 0.32548(6) 0.0248(6) Uani 1 1 d . . .
H21' H 0.5572 0.1932 0.3132 0.030 Uiso 1 1 calc . . R
C22' C 0.3816(3) 0.3327(3) 0.31493(7) 0.0274(7) Uani 1 1 d . . .
H22' H 0.3335 0.2967 0.2955 0.033 Uiso 1 1 calc . . R
C23' C 0.3199(3) 0.4476(3) 0.33323(7) 0.0300(7) Uani 1 1 d . . .
H23' H 0.2285 0.4907 0.3264 0.036 Uiso 1 1 calc . . R
C24' C 0.3914(3) 0.4997(3) 0.36163(6) 0.0239(6) Uani 1 1 d . . .
H24' H 0.3467 0.5786 0.3737 0.029 Uiso 1 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.370(3) . ?
O1 C14 1.425(3) . ?
O2 C12 1.370(3) . ?
O2 C15 1.423(4) . ?
N1 C1 1.348(3) . ?
N1 C5 1.346(3) . ?
N1 C16 1.490(3) . ?
C1 C2 1.362(4) . ?
C2 C3 1.388(4) . ?
C3 C4 1.407(4) . ?
C3 C6 1.475(4) . ?
C4 C5 1.377(4) . ?
C6 C7 1.310(4) . ?
C7 C8 1.486(4) . ?
C8 C9 1.383(4) . ?
C8 C13 1.388(4) . ?
C9 C10 1.399(4) . ?
C10 C11 1.377(4) . ?
C11 C12 1.409(4) . ?
C12 C13 1.370(4) . ?
C16 C17 1.505(4) . ?
B1 C1' 1.669(4) . ?
B1 C7' 1.648(4) . ?
B1 C13' 1.647(4) . ?
B1 C19' 1.647(4) . ?
C1' C2' 1.395(4) . ?
C1' C6' 1.403(3) . ?
C2' C3' 1.404(4) . ?
C3' C4' 1.375(4) . ?
C4' C5' 1.388(4) . ?
C5' C6' 1.399(4) . ?
C7' C8' 1.397(3) . ?
C7' C12' 1.402(3) . ?
C8' C9' 1.390(4) . ?
C9' C10' 1.380(4) . ?
C10' C11' 1.392(4) . ?
C11' C12' 1.394(4) . ?
C13' C14' 1.417(4) . ?
C13' C18' 1.397(4) . ?
C14' C15' 1.385(4) . ?
C15' C16' 1.386(4) . ?
C16' C17' 1.388(4) . ?
C17' C18' 1.391(4) . ?
C19' C20' 1.410(4) . ?
C19' C24' 1.401(4) . ?
C20' C21' 1.398(3) . ?
C21' C22' 1.374(4) . ?
C22' C23' 1.387(4) . ?
C23' C24' 1.390(4) . ?

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
C11 O1 C14 117.6(2) . . ?
C12 O2 C15 117.9(2) . . ?
C1 N1 C16 119.3(2) . . ?
C5 N1 C1 120.3(2) . . ?
C5 N1 C16 120.3(2) . . ?
N1 C1 C2 120.9(3) . . ?
C1 C2 C3 121.1(3) . . ?
C2 C3 C4 116.9(2) . . ?
C2 C3 C6 118.6(3) . . ?
C4 C3 C6 124.5(3) . . ?
C5 C4 C3 120.0(3) . . ?
N1 C5 C4 120.8(3) . . ?
C7 C6 C3 123.2(3) . . ?
C6 C7 C8 125.6(3) . . ?
C9 C8 C7 123.4(3) . . ?
C9 C8 C13 118.9(3) . . ?
C13 C8 C7 117.7(3) . . ?
C8 C9 C10 120.9(3) . . ?
C11 C10 C9 119.8(3) . . ?
O1 C11 C10 125.3(2) . . ?
O1 C11 C12 115.4(2) . . ?
C10 C11 C12 119.2(2) . . ?
O2 C12 C11 115.0(2) . . ?
C13 C12 O2 124.7(3) . . ?
C13 C12 C11 120.3(2) . . ?
C12 C13 C8 120.9(3) . . ?
N1 C16 C17 112.8(2) . . ?
C7' B1 C1' 107.0(2) . . ?
C13' B1 C1' 106.0(2) . . ?
C13' B1 C7' 111.1(2) . . ?
C19' B1 C1' 110.1(2) . . ?
C19' B1 C7' 110.4(2) . . ?
C19' B1 C13' 112.1(2) . . ?
C2' C1' B1 124.8(2) . . ?
C2' C1' C6' 115.3(2) . . ?
C6' C1' B1 119.9(2) . . ?
C1' C2' C3' 122.5(3) . . ?
C4' C3' C2' 120.3(3) . . ?
C3' C4' C5' 119.2(3) . . ?
C4' C5' C6' 119.6(3) . . ?
C5' C6' C1' 123.0(2) . . ?
C8' C7' B1 124.4(2) . . ?
C8' C7' C12' 115.3(2) . . ?
C12' C7' B1 120.3(2) . . ?
C9' C8' C7' 122.5(3) . . ?
C10' C9' C8' 120.8(3) . . ?
C9' C10' C11' 118.7(3) . . ?
C10' C11' C12' 119.6(3) . . ?
C11' C12' C7' 123.0(3) . . ?
C14' C13' B1 121.2(2) . . ?
C18' C13' B1 124.8(2) . . ?
C18' C13' C14' 113.9(2) . . ?
C15' C14' C13' 123.3(3) . . ?
C14' C15' C16' 120.5(3) . . ?
C15' C16' C17' 118.2(3) . . ?
C16' C17' C18' 120.4(3) . . ?
C17' C18' C13' 123.6(3) . . ?
C20' C19' B1 123.9(2) . . ?
C24' C19' B1 121.5(2) . . ?
C24' C19' C20' 114.6(2) . . ?
C21' C20' C19' 122.6(2) . . ?
C22' C21' C20' 120.6(3) . . ?
C21' C22' C23' 118.8(3) . . ?
C22' C23' C24' 120.2(3) . . ?
C23' C24' C19' 123.3(3) . . ?

_database_code_depnum_ccdc_archive 'CCDC 969552'
#######################################################################
#
#                 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_new
_audit_creation_date             2014-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H20 N O2, B F4'
_chemical_formula_sum            'C17 H20 B F4 N O2'
_chemical_formula_weight         357.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.3008(3)
_cell_length_b                   20.8807(6)
_cell_length_c                   11.3281(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.918(2)
_cell_angle_gamma                90.00
_cell_volume                     1725.95(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4125
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_correction_T_min  0.6413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0683 before and 0.0338 after correction.
The Ratio of minimum to maximum transmission is 0.8567.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13052
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.95
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2977
_reflns_number_total             4538
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4538
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0673P)²+0.4759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1478
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Others
 Fixed Sof: F1(0.6) F2(0.6) F3(0.6) F4(0.6) F1A(0.2) F2A(0.2) F3A(0.2)
 F4A(0.2) F1B(0.2) F2B(0.2) F3B(0.2) F4B(0.2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.3637(2) 0.63277(7) 0.62257(11) 0.0269(3) Uani 1 1 d . . .
O2 O 0.38558(19) 0.73757(6) 0.74677(12) 0.0284(3) Uani 1 1 d . . .
N1 N 0.2275(2) 0.34369(7) 1.30368(13) 0.0211(3) Uani 1 1 d . . .
C1 C 0.2250(3) 0.33630(10) 1.18529(16) 0.0223(4) Uani 1 1 d . . .
C2 C 0.1923(3) 0.38806(9) 1.11133(16) 0.0222(4) Uani 1 1 d . . .
C3 C 0.1570(3) 0.44845(9) 1.15910(16) 0.0216(4) Uani 1 1 d . . .
C4 C 0.1730(3) 0.45499(9) 1.28183(17) 0.0246(4) Uani 1 1 d . . .
C5 C 0.2074(3) 0.40220(10) 1.35233(17) 0.0246(4) Uani 1 1 d . . .
C6 C 0.0793(3) 0.50258(9) 1.08599(15) 0.0219(4) Uani 1 1 d . . .
C7 C 0.1315(3) 0.50803(9) 0.95499(15) 0.0211(4) Uani 1 1 d . . .
C8 C 0.2191(3) 0.56904(9) 0.91213(16) 0.0214(4) Uani 1 1 d . . .
C9 C 0.2655(3) 0.57043(9) 0.79191(16) 0.0224(4) Uani 1 1 d . . .
C10 C 0.3204(3) 0.62681(9) 0.73955(16) 0.0221(4) Uani 1 1 d . . .
C11 C 0.3339(3) 0.68394(9) 0.80715(17) 0.0228(4) Uani 1 1 d . . .
C12 C 0.2979(3) 0.68192(10) 0.92634(18) 0.0250(4) Uani 1 1 d . . .
C13 C 0.2387(3) 0.62444(9) 0.97797(17) 0.0250(4) Uani 1 1 d . . .
C14 C 0.3386(3) 0.57645(11) 0.55063(19) 0.0319(5) Uani 1 1 d . . .
C15 C 0.3716(3) 0.79758(10) 0.8084(2) 0.0335(5) Uani 1 1 d . . .
C16 C 0.2349(3) 0.28584(10) 1.38171(18) 0.0250(4) Uani 1 1 d . . .
C17 C 0.0423(3) 0.26372(11) 1.4044(2) 0.0304(5) Uani 1 1 d . . .
B1 B 0.1698(4) 0.37705(11) 0.6974(2) 0.0281(5) Uani 1 1 d . . .
F1 F 0.1792(6) 0.31390(17) 0.6547(3) 0.0279(10) Uiso 0.60 1 d A 1 .
F2 F 0.2188(5) 0.37449(12) 0.8167(2) 0.0253(6) Uiso 0.60 1 d A 1 .
F3 F 0.2926(7) 0.41448(19) 0.6376(3) 0.0321(9) Uiso 0.60 1 d A 1 .
F4 F 0.0000(6) 0.4030(2) 0.6846(4) 0.0469(11) Uiso 0.60 1 d A 1 .
F1A F 0.1292(10) 0.3152(3) 0.6449(6) 0.0168(17) Uiso 0.20 1 d A 2 .
F2A F 0.1515(10) 0.3757(3) 0.8143(6) 0.0235(17) Uiso 0.20 1 d A 2 .
F3A F 0.3324(17) 0.4116(6) 0.6488(11) 0.055(4) Uiso 0.20 1 d A 2 .
F4A F -0.0035(13) 0.4049(4) 0.6450(8) 0.043(2) Uiso 0.20 1 d A 2 .
F1B F 0.2108(12) 0.3224(4) 0.6399(7) 0.023(2) Uiso 0.20 1 d A 3 .
F2B F 0.2779(11) 0.3772(3) 0.8139(6) 0.0260(19) Uiso 0.20 1 d A 3 .
F3B F 0.2357(11) 0.4273(4) 0.6345(6) 0.032(2) Uiso 0.20 1 d A 3 .
F4B F -0.0332(12) 0.3905(4) 0.7035(8) 0.036(2) Uiso 0.20 1 d A 3 .
H1 H 0.243(3) 0.2951(11) 1.1602(18) 0.024(5) Uiso 1 1 d . . .
H2 H 0.191(3) 0.3790(10) 1.031(2) 0.025(6) Uiso 1 1 d . . .
H4 H 0.151(3) 0.4962(11) 1.3195(19) 0.029(6) Uiso 1 1 d . . .
H5 H 0.208(3) 0.4044(10) 1.4383(19) 0.024(5) Uiso 1 1 d . . .
H9 H 0.257(3) 0.5313(11) 0.745(2) 0.033(6) Uiso 1 1 d . . .
H12 H 0.312(3) 0.7185(10) 0.9724(18) 0.020(5) Uiso 1 1 d . . .
H13 H 0.207(3) 0.6268(11) 1.063(2) 0.037(6) Uiso 1 1 d . . .
H14A H 0.377(3) 0.5867(11) 0.472(2) 0.036(6) Uiso 1 1 d . . .
H14B H 0.205(4) 0.5612(13) 0.546(2) 0.045(7) Uiso 1 1 d . . .
H14C H 0.419(3) 0.5391(11) 0.5811(19) 0.032(6) Uiso 1 1 d . . .
H15A H 0.407(3) 0.8314(13) 0.754(2) 0.041(7) Uiso 1 1 d . . .
H15B H 0.458(3) 0.7991(11) 0.872(2) 0.035(6) Uiso 1 1 d . . .
H15C H 0.236(4) 0.8035(12) 0.830(2) 0.039(7) Uiso 1 1 d . . .
H16A H 0.301(3) 0.2983(11) 1.452(2) 0.031(6) Uiso 1 1 d . . .
H16B H 0.308(3) 0.2533(11) 1.345(2) 0.031(6) Uiso 1 1 d . . .
H17A H 0.048(3) 0.2250(11) 1.457(2) 0.031(6) Uiso 1 1 d . . .
H17B H -0.020(3) 0.2496(11) 1.332(2) 0.035(6) Uiso 1 1 d . . .
H17C H -0.028(3) 0.3000(12) 1.442(2) 0.036(6) Uiso 1 1 d . . .
H6 H 0.094(3) 0.5436(11) 1.1302(18) 0.026(6) Uiso 1 1 d . . .
H7 H 0.203(3) 0.4712(10) 0.9298(16) 0.015(5) 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
O1 C10 1.378(2) . ?
O1 C14 1.439(3) . ?
O2 C11 1.372(2) . ?
O2 C15 1.439(3) . ?
N1 C1 1.349(2) . ?
N1 C5 1.350(3) . ?
N1 C16 1.497(2) . ?
C1 C2 1.383(3) . ?
C1 H1 0.92(2) . ?
C2 C3 1.399(3) . ?
C2 H2 0.93(2) . ?
C3 C4 1.398(3) . ?
C3 C6 1.501(3) . ?
C4 C5 1.379(3) . ?
C4 H4 0.98(2) . ?
C5 H5 0.97(2) . ?
C6 C7 1.608(3) 3_567 ?
C6 C7 1.549(2) . ?
C6 H6 1.00(2) . ?
C7 C6 1.608(3) 3_567 ?
C7 C8 1.513(3) . ?
C7 H7 0.98(2) . ?
C8 C9 1.415(3) . ?
C8 C13 1.381(3) . ?
C9 C10 1.383(3) . ?
C9 H9 0.97(2) . ?
C10 C11 1.419(3) . ?
C11 C12 1.385(3) . ?
C12 C13 1.409(3) . ?
C12 H12 0.93(2) . ?
C13 H13 0.99(2) . ?
C14 H14A 0.97(2) . ?
C14 H14B 1.02(3) . ?
C14 H14C 1.03(2) . ?
C15 H15A 0.98(3) . ?
C15 H15B 0.95(3) . ?
C15 H15C 1.04(3) . ?
C16 C17 1.511(3) . ?
C16 H16A 0.95(2) . ?
C16 H16B 0.97(2) . ?
C17 H17A 1.00(2) . ?
C17 H17B 0.98(2) . ?
C17 H17C 1.02(2) . ?
B1 F1 1.407(4) . ?
B1 F2 1.387(3) . ?
B1 F3 1.384(5) . ?
B1 F4 1.356(5) . ?
B1 F1A 1.449(7) . ?
B1 F2A 1.335(7) . ?
B1 F3A 1.509(13) . ?
B1 F4A 1.497(9) . ?
B1 F1B 1.352(8) . ?
B1 F2B 1.515(8) . ?
B1 F3B 1.365(8) . ?
B1 F4B 1.512(9) . ?

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
C10 O1 C14 116.22(15) . . ?
C11 O2 C15 116.35(16) . . ?
C1 N1 C5 120.73(16) . . ?
C1 N1 C16 119.59(16) . . ?
C5 N1 C16 119.43(16) . . ?
N1 C1 C2 120.59(18) . . ?
N1 C1 H1 114.7(13) . . ?
C2 C1 H1 124.7(13) . . ?
C1 C2 C3 120.01(17) . . ?
C1 C2 H2 115.5(13) . . ?
C3 C2 H2 124.4(13) . . ?
C2 C3 C6 122.42(16) . . ?
C4 C3 C2 117.52(17) . . ?
C4 C3 C6 119.52(17) . . ?
C3 C4 H4 120.8(13) . . ?
C5 C4 C3 120.36(18) . . ?
C5 C4 H4 118.7(13) . . ?
N1 C5 C4 120.46(17) . . ?
N1 C5 H5 117.0(12) . . ?
C4 C5 H5 122.4(13) . . ?
C3 C6 C7 113.31(15) . 3_567 ?
C3 C6 C7 118.91(16) . . ?
C3 C6 H6 109.7(12) . . ?
C7 C6 C7 89.85(13) . 3_567 ?
C7 C6 H6 110.5(12) 3_567 . ?
C7 C6 H6 113.1(12) . . ?
C6 C7 C6 90.15(13) . 3_567 ?
C6 C7 H7 111.9(11) . . ?
C6 C7 H7 108.8(12) 3_567 . ?
C8 C7 C6 119.32(15) . . ?
C8 C7 C6 115.73(15) . 3_567 ?
C8 C7 H7 109.5(11) . . ?
C9 C8 C7 116.34(16) . . ?
C13 C8 C7 124.70(16) . . ?
C13 C8 C9 118.61(17) . . ?
C8 C9 H9 119.5(14) . . ?
C10 C9 C8 120.82(18) . . ?
C10 C9 H9 119.7(13) . . ?
O1 C10 C9 124.62(17) . . ?
O1 C10 C11 115.40(16) . . ?
C9 C10 C11 119.98(17) . . ?
O2 C11 C10 115.62(16) . . ?
O2 C11 C12 125.13(17) . . ?
C12 C11 C10 119.24(17) . . ?
C11 C12 C13 120.10(18) . . ?
C11 C12 H12 120.1(13) . . ?
C13 C12 H12 119.8(13) . . ?
C8 C13 C12 121.11(18) . . ?
C8 C13 H13 122.5(14) . . ?
C12 C13 H13 116.3(14) . . ?
O1 C14 H14A 107.8(14) . . ?
O1 C14 H14B 112.6(15) . . ?
O1 C14 H14C 111.7(13) . . ?
H14A C14 H14B 109(2) . . ?
H14A C14 H14C 107.2(19) . . ?
H14B C14 H14C 108.1(19) . . ?
O2 C15 H15A 107.2(15) . . ?
O2 C15 H15B 110.1(15) . . ?
O2 C15 H15C 107.7(14) . . ?
H15A C15 H15B 106(2) . . ?
H15A C15 H15C 110(2) . . ?
H15B C15 H15C 116(2) . . ?
N1 C16 C17 109.39(16) . . ?
N1 C16 H16A 106.3(14) . . ?
N1 C16 H16B 108.8(14) . . ?
C17 C16 H16A 112.8(14) . . ?
C17 C16 H16B 112.8(14) . . ?
H16A C16 H16B 107(2) . . ?
C16 C17 H17A 109.0(13) . . ?
C16 C17 H17B 111.1(14) . . ?
C16 C17 H17C 109.1(14) . . ?
H17A C17 H17B 105.3(19) . . ?
H17A C17 H17C 111.5(19) . . ?
H17B C17 H17C 111(2) . . ?
F2 B1 F1 106.5(2) . . ?
F3 B1 F1 108.7(3) . . ?
F3 B1 F2 110.4(3) . . ?
F4 B1 F1 113.1(3) . . ?
F4 B1 F2 108.9(3) . . ?
F4 B1 F3 109.1(3) . . ?
F2A B1 F1A 111.3(4) . . ?
F2A B1 F3A 118.6(6) . . ?
F2A B1 F4A 106.9(5) . . ?
F4A B1 F3A 109.5(6) . . ?
F1B B1 F3B 108.0(5) . . ?
F1B B1 F4B 114.3(5) . . ?
F3B B1 F2B 105.7(5) . . ?
F3B B1 F4B 104.2(5) . . ?
F4B B1 F2B 116.3(5) . . ?

_database_code_depnum_ccdc_archive 'CCDC 859814'
#######################################################################
#
#                 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_new
_audit_creation_date             2014-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H20 N O2, B F4'
_chemical_formula_sum            'C17 H20 B F4 N O2'
_chemical_formula_weight         357.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.319(2)
_cell_length_b                   20.852(7)
_cell_length_c                   11.302(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.835(5)
_cell_angle_gamma                90.00
_cell_volume                     1723.9(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3417
_cell_measurement_temperature    170.2(2)
_cell_measurement_theta_max      23.92
_cell_measurement_theta_min      2.66
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9635
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17378
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.05
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3028
_reflns_number_total             4156
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0601
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0922P)²+0.4961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1668
_refine_ls_wR_factor_ref         0.1791
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(O2A)=Sof(O1A)=Sof(N1A)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=
 Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=
 Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(C12A)=Sof(C13A)=
 Sof(H13A)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(C14A)=Sof(H14D)=
 Sof(H14E)=Sof(H14F)=Sof(H16C)=Sof(H16D)=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(N1)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(C4)=
 Sof(H4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(C9)=
 Sof(H9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(C12)=Sof(C13)=Sof(H13)=Sof(C14)=
 Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(H16A)=
 Sof(H16B)=FVAR(1)
 Fixed Sof: F1(0.24) F2(0.24) F3(0.24) F4(0.24) F1A(0.38) F2A(0.38) F3A(0.38)
 F4A(0.38) F1B(0.38) F2B(0.38) F3B(0.38) F4B(0.38)
3.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C6A(H6A), C7A(H7A)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C16(H16C,H16D)
3.c Me refined with riding coordinates:
 C15(H15A,H15B,H15C), C15A(H15D,H15E,H15F)
3.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C13(H13), C1A(H1A),
 C2A(H2A), C4A(H4A), C5A(H5A), C9A(H9A), C10A(H10A), C13A(H13A)
3.e Fitted hexagon refined as free rotating group:
 N1A(C1A,C2A,C3A,C4A,C5A)
3.f Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C14A(H14D,H14E,H14F), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.6167(9) 0.2367(3) 0.2531(6) 0.0390(10) Uani 0.898(4) 1 d A 1 .
O2 O 0.6372(3) 0.13276(10) 0.3772(2) 0.0367(6) Uani 0.898(4) 1 d A 1 .
N1 N 0.7712(6) -0.15582(13) -0.3021(3) 0.030(2) Uani 0.898(4) 1 d A 1 .
C1 C 0.7924(4) -0.09780(13) -0.3505(4) 0.0335(7) Uani 0.898(4) 1 d A 1 .
H1 H 0.7828 -0.0932 -0.4341 0.040 Uiso 0.898(4) 1 calc A 1 R
C2 C 0.8277(3) -0.04500(11) -0.2815(2) 0.0338(5) Uani 0.898(4) 1 d A 1 .
H2 H 0.8416 -0.0041 -0.3173 0.041 Uiso 0.898(4) 1 calc A 1 R
C3 C 0.8432(3) -0.05122(11) -0.1585(2) 0.0283(5) Uani 0.898(4) 1 d A 1 .
C4 C 0.8065(3) -0.11148(13) -0.11073(19) 0.0310(5) Uani 0.898(4) 1 d A 1 .
H4 H 0.8047 -0.1171 -0.0274 0.037 Uiso 0.898(4) 1 calc A 1 R
C5 C 0.7734(5) -0.16212(18) -0.1845(3) 0.0325(7) Uani 0.898(4) 1 d A 1 .
H5 H 0.7512 -0.2031 -0.1513 0.039 Uiso 0.898(4) 1 calc A 1 R
C6 C 0.9214(3) 0.00232(9) -0.08547(17) 0.0287(5) Uani 0.898(4) 1 d . 1 .
H6 H 0.9048 0.0443 -0.1274 0.034 Uiso 0.898(4) 1 calc A 1 R
C7 C 0.8694(3) 0.00823(9) 0.04562(16) 0.0285(5) Uani 0.898(4) 1 d . 1 .
H7 H 0.7950 -0.0297 0.0689 0.034 Uiso 0.898(4) 1 calc A 1 R
C8 C 0.7825(3) 0.06900(11) 0.0882(2) 0.0282(5) Uani 0.898(4) 1 d A 1 .
C9 C 0.7641(3) 0.12405(15) 0.0226(2) 0.0334(5) Uani 0.898(4) 1 d A 1 .
H9 H 0.7908 0.1234 -0.0591 0.040 Uiso 0.898(4) 1 calc A 1 R
C10 C 0.7062(4) 0.18125(17) 0.0744(3) 0.0354(7) Uani 0.898(4) 1 d A 1 .
H10 H 0.6922 0.2186 0.0269 0.042 Uiso 0.898(4) 1 calc A 1 R
C11 C 0.6690(4) 0.18430(14) 0.1939(3) 0.0302(7) Uani 0.898(4) 1 d A 1 .
C12 C 0.6814(4) 0.12660(16) 0.2599(3) 0.0299(7) Uani 0.898(4) 1 d A 1 .
C13 C 0.7354(3) 0.07081(10) 0.2082(2) 0.0289(5) Uani 0.898(4) 1 d A 1 .
H13 H 0.7414 0.0326 0.2539 0.035 Uiso 0.898(4) 1 calc A 1 R
C14 C 0.6247(6) 0.2971(2) 0.1926(4) 0.0475(10) Uani 0.898(4) 1 d A 1 .
H14A H 0.5406 0.2964 0.1234 0.071 Uiso 0.898(4) 1 calc A 1 GR
H14B H 0.7495 0.3046 0.1669 0.071 Uiso 0.898(4) 1 calc A 1 GR
H14C H 0.5894 0.3315 0.2462 0.071 Uiso 0.898(4) 1 calc A 1 GR
C15 C 0.6618(4) 0.07717(13) 0.4485(2) 0.0431(6) Uani 0.898(4) 1 d A 1 .
H15A H 0.6260 0.0866 0.5295 0.065 Uiso 0.898(4) 1 calc A 1 R
H15B H 0.7906 0.0642 0.4493 0.065 Uiso 0.898(4) 1 calc A 1 R
H15C H 0.5857 0.0423 0.4161 0.065 Uiso 0.898(4) 1 calc A 1 R
O2A O 0.659(3) 0.1279(10) 0.343(2) 0.028(5) Uiso 0.102(4) 1 d A 2 .
O1A O 0.622(8) 0.246(2) 0.245(5) 0.036(10) Uiso 0.102(4) 1 d A 2 .
N1A N 0.760(4) -0.1571(9) -0.2967(16) 0.04(2) Uiso 0.102(4) 1 d A 2 .
C1A C 0.785(4) -0.0926(10) -0.3229(14) 0.059(17) Uiso 0.102(4) 1 d A 2 G
H1A H 0.7854 -0.0788 -0.4030 0.071 Uiso 0.102(4) 1 calc A 2 R
C2A C 0.810(2) -0.0483(6) -0.2319(19) 0.020(4) Uiso 0.102(4) 1 d A 2 G
H2A H 0.8272 -0.0043 -0.2498 0.024 Uiso 0.102(4) 1 calc A 2 R
C3A C 0.810(2) -0.0685(8) -0.1147(16) 0.025(4) Uiso 0.102(4) 1 d A 2 G
C4A C 0.784(3) -0.1330(9) -0.0885(14) 0.060(10) Uiso 0.102(4) 1 d A 2 G
H4A H 0.7842 -0.1468 -0.0084 0.072 Uiso 0.102(4) 1 calc A 2 R
C5A C 0.760(3) -0.1773(6) -0.1795(19) 0.010(5) Uiso 0.102(4) 1 d A 2 G
H5A H 0.7424 -0.2213 -0.1616 0.012 Uiso 0.102(4) 1 calc A 2 R
C6A C 0.874(3) -0.0259(10) -0.0131(18) 0.035(5) Uiso 0.102(4) 1 d . 2 .
H6A H 0.7920 -0.0314 0.0555 0.042 Uiso 0.102(4) 1 calc A 2 R
C7A C 0.915(2) 0.0396(9) -0.0282(16) 0.031(5) Uiso 0.102(4) 1 d . 2 .
H7A H 0.9075 0.0512 -0.1141 0.037 Uiso 0.102(4) 1 calc A 2 R
C8A C 0.816(3) 0.0907(12) 0.046(2) 0.023(4) Uiso 0.102(4) 1 d A 2 .
C9A C 0.777(3) 0.1470(13) -0.005(2) 0.036(6) Uiso 0.102(4) 1 d A 2 .
H9A H 0.7967 0.1515 -0.0871 0.043 Uiso 0.102(4) 1 calc A 2 R
C10A C 0.710(4) 0.1979(13) 0.053(3) 0.024(6) Uiso 0.102(4) 1 d A 2 .
H10A H 0.6976 0.2398 0.0213 0.029 Uiso 0.102(4) 1 calc A 2 R
C11A C 0.668(4) 0.1819(15) 0.158(3) 0.025(7) Uiso 0.102(4) 1 d A 2 .
C12A C 0.701(5) 0.136(2) 0.232(4) 0.041(11) Uiso 0.102(4) 1 d A 2 .
C13A C 0.769(2) 0.0788(8) 0.158(2) 0.017(4) Uiso 0.102(4) 1 d A 2 .
H13A H 0.7771 0.0369 0.1905 0.021 Uiso 0.102(4) 1 calc A 2 R
C15A C 0.686(5) 0.0600(17) 0.399(4) 0.076(10) Uiso 0.102(4) 1 d A 2 .
H15D H 0.6462 0.0607 0.4809 0.113 Uiso 0.102(4) 1 calc A 2 R
H15E H 0.8156 0.0482 0.3978 0.113 Uiso 0.102(4) 1 calc A 2 R
H15F H 0.6135 0.0285 0.3535 0.113 Uiso 0.102(4) 1 calc A 2 R
C14A C 0.671(4) 0.3007(18) 0.188(3) 0.020(6) Uiso 0.102(4) 1 d A 2 .
H14D H 0.5828 0.3093 0.1225 0.030 Uiso 0.102(4) 1 calc A 2 GR
H14E H 0.7931 0.2953 0.1562 0.030 Uiso 0.102(4) 1 calc A 2 GR
H14F H 0.6720 0.3369 0.2433 0.030 Uiso 0.102(4) 1 calc A 2 GR
C16 C 0.7625(3) -0.21277(10) -0.38064(17) 0.0375(5) Uani 1 1 d . . .
H16A H 0.6987 -0.2016 -0.4564 0.045 Uiso 0.898(4) 1 calc A 1 R
H16B H 0.6930 -0.2475 -0.3427 0.045 Uiso 0.898(4) 1 calc A 1 R
H16C H 0.7017 -0.2001 -0.4566 0.045 Uiso 0.102(4) 1 calc A 2 R
H16D H 0.6920 -0.2487 -0.3473 0.045 Uiso 0.102(4) 1 calc A 2 R
C17 C 0.9534(3) -0.23527(11) -0.4035(2) 0.0444(5) Uani 1 1 d A . .
H17A H 1.0220 -0.2005 -0.4401 0.067 Uiso 1 1 calc . . GR
H17B H 0.9482 -0.2723 -0.4569 0.067 Uiso 1 1 calc . . GR
H17C H 1.0145 -0.2476 -0.3285 0.067 Uiso 1 1 calc . . GR
B1 B 0.1711(4) 0.37794(12) 0.1954(2) 0.0407(6) Uani 1 1 d . . .
F1 F 0.1906(12) 0.3112(3) 0.1641(6) 0.0293(16) Uiso 0.24 1 d B 1 .
F2 F 0.2289(11) 0.3721(3) 0.3162(5) 0.0165(11) Uiso 0.24 1 d B 1 .
F3 F 0.3032(12) 0.4073(3) 0.1258(6) 0.0323(15) Uiso 0.24 1 d B 1 .
F4 F 0.0301(12) 0.4141(4) 0.1874(9) 0.064(2) Uiso 0.24 1 d B 1 .
F1A F 0.2079(7) 0.3227(2) 0.1417(4) 0.0404(12) Uiso 0.38 1 d B 2 .
F2A F 0.2676(7) 0.3815(3) 0.3094(5) 0.0576(19) Uiso 0.38 1 d B 2 .
F3A F 0.2444(7) 0.4236(3) 0.1315(5) 0.0617(13) Uiso 0.38 1 d B 2 .
F4A F -0.0203(6) 0.3938(2) 0.2009(4) 0.0520(11) Uiso 0.38 1 d B 2 .
F1B F 0.1384(6) 0.3156(2) 0.1484(4) 0.0345(10) Uiso 0.38 1 d B 3 .
F2B F 0.1675(7) 0.3768(2) 0.3121(4) 0.0509(14) Uiso 0.38 1 d B 3 .
F3B F 0.3190(9) 0.4159(3) 0.1503(6) 0.064(2) Uiso 0.38 1 d B 3 .
F4B F -0.0004(9) 0.4039(3) 0.1519(5) 0.0698(16) Uiso 0.38 1 d B 3 .


_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 C11 1.343(7) . ?
O1 C14 1.435(7) . ?
O2 C12 1.380(4) . ?
O2 C15 1.420(3) . ?
N1 C1 1.339(4) . ?
N1 C5 1.335(3) . ?
N1 C16 1.483(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.369(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(3) . ?
C3 C4 1.397(3) . ?
C3 C6 1.492(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.362(4) . ?
C5 H5 0.9500 . ?
C6 H6 1.0000 . ?
C6 C7 1.597(3) 3_755 ?
C6 C7 1.546(3) . ?
C7 C6 1.597(3) 3_755 ?
C7 H7 1.0000 . ?
C7 C8 1.504(3) . ?
C8 C9 1.371(3) . ?
C8 C13 1.411(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.400(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(4) . ?
C11 C12 1.417(5) . ?
C12 C13 1.366(4) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O2A C12A 1.31(3) . ?
O2A C15A 1.56(4) . ?
O1A C11A 1.71(6) . ?
O1A C14A 1.36(7) . ?
N1A C1A 1.3900 . ?
N1A C5A 1.3900 . ?
N1A C16 1.500(13) . ?
C1A H1A 0.9500 . ?
C1A C2A 1.3900 . ?
C2A H2A 0.9500 . ?
C2A C3A 1.3900 . ?
C3A C4A 1.3900 . ?
C3A C6A 1.51(2) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.3900 . ?
C5A H5A 0.9500 . ?
C6A H6A 1.0000 . ?
C6A C7A 1.41(3) . ?
C6A C7A 1.63(3) 3_755 ?
C7A C6A 1.63(3) 3_755 ?
C7A H7A 1.0000 . ?
C7A C8A 1.55(3) . ?
C8A C9A 1.33(3) . ?
C8A C13A 1.35(3) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.35(4) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.27(4) . ?
C11A C12A 1.29(5) . ?
C12A C13A 1.55(5) . ?
C13A H13A 0.9500 . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 H16C 0.9900 . ?
C16 H16D 0.9900 . ?
C16 C17 1.505(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
B1 F1 1.444(7) . ?
B1 F2 1.422(6) . ?
B1 F3 1.406(7) . ?
B1 F4 1.278(9) . ?
B1 F1A 1.333(5) . ?
B1 F2A 1.452(6) . ?
B1 F3A 1.319(5) . ?
B1 F4A 1.442(5) . ?
B1 F1B 1.421(4) . ?
B1 F2B 1.321(5) . ?
B1 F3B 1.447(7) . ?
B1 F4B 1.439(6) . ?

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
C11 O1 C14 117.4(5) . . ?
C12 O2 C15 116.1(3) . . ?
C1 N1 C16 118.8(3) . . ?
C5 N1 C1 119.9(3) . . ?
C5 N1 C16 121.1(3) . . ?
N1 C1 H1 119.5 . . ?
N1 C1 C2 121.1(3) . . ?
C2 C1 H1 119.5 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C6 119.9(2) . . ?
C4 C3 C2 117.24(18) . . ?
C4 C3 C6 122.3(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 122.0(3) . . ?
N1 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C3 C6 H6 110.7 . . ?
C3 C6 C7 113.59(16) . 3_755 ?
C3 C6 C7 119.22(18) . . ?
C7 C6 H6 110.7 3_755 . ?
C7 C6 H6 110.7 . . ?
C7 C6 C7 90.21(15) . 3_755 ?
C6 C7 C6 89.79(15) . 3_755 ?
C6 C7 H7 110.0 . . ?
C6 C7 H7 110.0 3_755 . ?
C8 C7 C6 119.54(18) . . ?
C8 C7 C6 115.93(16) . 3_755 ?
C8 C7 H7 110.0 . . ?
C9 C8 C7 124.6(2) . . ?
C9 C8 C13 118.3(2) . . ?
C13 C8 C7 116.7(2) . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.9(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
O1 C11 C10 126.2(4) . . ?
O1 C11 C12 116.3(4) . . ?
C10 C11 C12 117.5(3) . . ?
O2 C12 C11 114.4(3) . . ?
C13 C12 O2 124.8(3) . . ?
C13 C12 C11 120.8(3) . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.1(3) . . ?
C12 C13 H13 119.4 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12A O2A C15A 119(3) . . ?
C14A O1A C11A 109(4) . . ?
C1A N1A C5A 120.0 . . ?
C1A N1A C16 127.6(14) . . ?
C5A N1A C16 111.6(14) . . ?
N1A C1A H1A 120.0 . . ?
C2A C1A N1A 120.0 . . ?
C2A C1A H1A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C1A C2A C3A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C2A C3A C6A 122.3(15) . . ?
C4A C3A C6A 116.5(15) . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A C3A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
N1A C5A H5A 120.0 . . ?
C4A C5A N1A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C3A C6A H6A 110.0 . . ?
C7A C6A C3A 122.6(18) . . ?
C7A C6A H6A 110.0 3_755 . ?
C7A C6A H6A 110.0 . . ?
C6A C7A H7A 110.2 3_755 . ?
C6A C7A H7A 110.2 . . ?
C6A C7A C8A 119.5(18) . . ?
C8A C7A H7A 110.2 . . ?
C9A C8A C7A 118(2) . . ?
C9A C8A C13A 120.6(19) . . ?
C13A C8A C7A 121(2) . . ?
C8A C9A H9A 118.0 . . ?
C8A C9A C10A 124(2) . . ?
C10A C9A H9A 118.0 . . ?
C9A C10A H10A 124.8 . . ?
C11A C10A C9A 110(3) . . ?
C11A C10A H10A 124.8 . . ?
C10A C11A O1A 113(3) . . ?
C10A C11A C12A 139(3) . . ?
C12A C11A O1A 104(3) . . ?
O2A C12A C13A 120(3) . . ?
C11A C12A O2A 133(4) . . ?
C11A C12A C13A 106(3) . . ?
C8A C13A C12A 117(2) . . ?
C8A C13A H13A 121.3 . . ?
C12A C13A H13A 121.3 . . ?
O2A C15A H15D 109.5 . . ?
O2A C15A H15E 109.5 . . ?
O2A C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
O1A C14A H14D 109.5 . . ?
O1A C14A H14E 109.5 . . ?
O1A C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
N1 C16 N1A 4.1(12) . . ?
N1 C16 H16A 109.8 . . ?
N1 C16 H16B 109.8 . . ?
N1 C16 H16C 108.4 . . ?
N1 C16 H16D 113.0 . . ?
N1 C16 C17 109.3(2) . . ?
N1A C16 H16A 110.5 . . ?
N1A C16 H16B 106.0 . . ?
N1A C16 H16C 109.1 . . ?
N1A C16 H16D 109.1 . . ?
N1A C16 C17 112.3(13) . . ?
H16A C16 H16B 108.3 . . ?
H16A C16 H16D 105.7 . . ?
H16B C16 H16C 110.4 . . ?
H16C C16 H16D 107.9 . . ?
C17 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
C17 C16 H16C 109.1 . . ?
C17 C16 H16D 109.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
F2 B1 F1 97.1(4) . . ?
F3 B1 F1 102.0(5) . . ?
F3 B1 F2 112.7(5) . . ?
F4 B1 F1 129.6(6) . . ?
F4 B1 F2 109.4(6) . . ?
F4 B1 F3 105.8(6) . . ?
F1A B1 F1 14.8(3) . . ?
F1A B1 F2A 110.4(4) . . ?
F1A B1 F4A 115.4(4) . . ?
F3A B1 F1A 106.4(4) . . ?
F3A B1 F2A 104.7(4) . . ?
F3A B1 F4A 105.7(4) . . ?
F4A B1 F2A 113.3(3) . . ?
F1B B1 F4B 94.7(4) . . ?
F2B B1 F1B 110.4(3) . . ?
F2B B1 F3B 113.6(4) . . ?
F2B B1 F4B 107.6(4) . . ?
F4B B1 F3B 109.1(4) . . ?

_database_code_depnum_ccdc_archive 'CCDC 859815'
