#------------------------------------------------------------------------------
#$Date: 2017-08-17 05:26:49 +0300 (Thu, 17 Aug 2017) $
#$Revision: 199805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/89/7228917.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7228917
loop_
_publ_author_name
'Helttunen, Kaisa'
'Annala, Riia'
'Suhonen, Aku'
'Nauha, Elisa'
'Linnanto, Juha'
'Nissinen, Maija'
_publ_section_title
;
 Supramolecular chirality and symmetry breaking of fluoride complexes of
 achiral foldamers
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01109A
_journal_year                    2017
_chemical_formula_moiety         'C26 H20 N4 O3, C16 H36 N, F'
_chemical_formula_sum            'C42 H56 F N5 O3'
_chemical_formula_weight         697.91
_chemical_name_common
'N2-(2-benzamidophenyl)-N6-phenylpyridine-2,6-dicarboxamide tetra-butyl ammonium fluoride complex'
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-08-04 deposited with the CCDC.
2017-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.1554(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.94745(5)
_cell_length_b                   15.10359(11)
_cell_length_c                   14.92421(9)
_cell_measurement_reflns_used    46667
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      76.5380
_cell_measurement_theta_min      5.1150
_cell_volume                     1937.19(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 5.1977
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            77272
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.827
_diffrn_reflns_theta_min         4.252
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0549P)²+0.3902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3951
_reflns_number_total             4229
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01109a2.cif
_cod_data_source_block           5-TBAF
_cod_database_code               7228917
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.792
_shelx_estimated_absorpt_t_max   0.957
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.02850(8) 0.7500 0.26427(5) 0.03494(18) Uani 1 2 d S T P . .
O2 O 0.23408(9) 0.95079(5) 0.07326(5) 0.04651(19) Uani 1 1 d . . . . .
N2 N 0.11458(9) 0.84276(5) 0.13532(5) 0.03236(18) Uani 1 1 d . . . . .
H2N H 0.0937(13) 0.8191(8) 0.1869(8) 0.039 Uiso 1 1 d . U . . .
O1 O 0.2317(2) 0.95554(12) 0.53597(10) 0.0548(4) Uani 0.5 1 d . . P A -1
N1 N 0.10444(17) 0.85004(11) 0.43212(10) 0.0313(3) Uani 0.5 1 d . . P A -1
H1N H 0.089(3) 0.8282(15) 0.3731(16) 0.038 Uiso 0.5 1 d . U P B -1
C11 C 0.1939(2) 0.92283(14) 0.45808(13) 0.0385(4) Uani 0.5 1 d . . P A -1
N5 N 0.20826(11) 0.92644(6) 0.30578(8) 0.0452(2) Uani 0.5 1 d . . P A 1
C1 C 0.20826(11) 0.92644(6) 0.30578(8) 0.0452(2) Uani 0.5 1 d . . P A 2
H1 H 0.1408 0.8767 0.2966 0.054 Uiso 0.5 1 calc R U P A 2
C2 C 0.25874(15) 0.96522(8) 0.39152(10) 0.0546(3) Uani 1 1 d . . . . .
H2A H 0.2256 0.9418 0.4419 0.066 Uiso 0.5 1 calc R U P A 2
C3 C 0.35711(17) 1.03783(8) 0.40675(9) 0.0565(3) Uani 1 1 d . . . . .
H3 H 0.3901 1.0645 0.4667 0.068 Uiso 1 1 calc R U . . .
C4 C 0.40646(15) 1.07083(8) 0.33366(9) 0.0529(3) Uani 1 1 d . . . . .
H4 H 0.4756 1.1199 0.3430 0.063 Uiso 1 1 calc R U . . .
C5 C 0.35454(13) 1.03201(7) 0.24661(8) 0.0436(2) Uani 1 1 d . . . . .
H5 H 0.3864 1.0546 0.1954 0.052 Uiso 1 1 calc R U . . .
C6 C 0.25497(11) 0.95938(6) 0.23497(7) 0.0372(2) Uani 1 1 d . . . . .
C7 C 0.19940(11) 0.91773(6) 0.14007(7) 0.0357(2) Uani 1 1 d . . . . .
C8 C 0.04796(10) 0.79647(6) 0.05090(6) 0.03036(19) Uani 1 1 d . . . . .
C9 C -0.02328(11) 0.84192(7) -0.03141(6) 0.0379(2) Uani 1 1 d . . . . .
H9 H -0.0253 0.9048 -0.0316 0.046 Uiso 1 1 calc R U . . .
C10 C -0.09090(11) 0.79579(8) -0.11255(7) 0.0431(2) Uani 1 1 d . . . . .
H10 H -0.1376 0.8271 -0.1685 0.052 Uiso 1 1 calc R U . . .
C28 C 0.0435(7) 0.8014(4) 0.4928(4) 0.0322(9) Uani 0.5 1 d . . P A -1
C33 C 0.0101(7) 0.7127(4) 0.4732(4) 0.0375(10) Uani 0.5 1 d . . P A -1
H33 H 0.0320 0.6877 0.4198 0.045 Uiso 0.5 1 calc R U P A -1
C32 C -0.0535(4) 0.65916(19) 0.5278(2) 0.0503(6) Uani 0.5 1 d . . P A -1
H32 H -0.0769 0.5990 0.5112 0.060 Uiso 0.5 1 calc R U P A -1
C31 C -0.0826(7) 0.6935(4) 0.6066(3) 0.0477(10) Uani 0.5 1 d . . P A -1
H31 H -0.1217 0.6568 0.6466 0.057 Uiso 0.5 1 calc R U P A -1
C30 C -0.0544(7) 0.7817(4) 0.6267(4) 0.0468(12) Uani 0.5 1 d . . P A -1
H30 H -0.0779 0.8061 0.6798 0.056 Uiso 0.5 1 calc R U P A -1
C29 C 0.0082(3) 0.83646(18) 0.57069(17) 0.0403(5) Uani 0.5 1 d . . P A -1
H29 H 0.0265 0.8973 0.5858 0.048 Uiso 0.5 1 calc R U P A -1
N7 N 0.59788(12) 0.7500 0.12433(7) 0.0334(2) Uani 1 2 d S T P . .
C34A C 0.6982(9) 0.6752(7) 0.1271(7) 0.0324(14) Uani 0.5 1 d . . P C -1
H34A H 0.7900 0.6790 0.1823 0.039 Uiso 0.5 1 calc R U P C -1
H34B H 0.7348 0.6737 0.0704 0.039 Uiso 0.5 1 calc R U P C -1
C34B C 0.6989(9) 0.8355(7) 0.1195(7) 0.0378(19) Uani 0.5 1 d . . P C -1
H34C H 0.7818 0.8376 0.1793 0.045 Uiso 0.5 1 calc R U P C -1
H34D H 0.7515 0.8234 0.0705 0.045 Uiso 0.5 1 calc R U P C -1
C35A C 0.5998(3) 0.58829(18) 0.1328(2) 0.0395(6) Uani 0.5 1 d . . P C -1
H35A H 0.5589 0.5918 0.1879 0.047 Uiso 0.5 1 calc R U P C -1
H35B H 0.5103 0.5839 0.0764 0.047 Uiso 0.5 1 calc R U P C -1
C36A C 0.7030(4) 0.5063(3) 0.1404(3) 0.0471(7) Uani 0.5 1 d . . P C -1
H36A H 0.6353 0.4534 0.1259 0.057 Uiso 0.5 1 calc R U P C -1
H36B H 0.7600 0.5104 0.0924 0.057 Uiso 0.5 1 calc R U P C -1
C35B C 0.6375(3) 0.92475(19) 0.1027(2) 0.0444(6) Uani 0.5 1 d . . P C -1
H35C H 0.5587 0.9337 0.1370 0.053 Uiso 0.5 1 calc R U P C -1
H35D H 0.5852 0.9321 0.0353 0.053 Uiso 0.5 1 calc R U P C -1
C36B C 0.7637(4) 0.9945(3) 0.1331(3) 0.0497(8) Uani 0.5 1 d . . P C -1
H36C H 0.7222 1.0526 0.1068 0.060 Uiso 0.5 1 calc R U P C -1
H36D H 0.8519 0.9792 0.1081 0.060 Uiso 0.5 1 calc R U P C -1
C37A C 0.8171(9) 0.4932(5) 0.2321(6) 0.063(2) Uani 0.5 1 d . . P C -1
H37A H 0.8752 0.5482 0.2514 0.095 Uiso 0.5 1 calc R U P C -1
H37B H 0.8894 0.4458 0.2275 0.095 Uiso 0.5 1 calc R U P C -1
H37C H 0.7624 0.4769 0.2782 0.095 Uiso 0.5 1 calc R U P C -1
C37B C 0.8221(8) 1.0016(5) 0.2396(6) 0.066(3) Uani 0.5 1 d . . P C -1
H37D H 0.8790 0.9476 0.2650 0.099 Uiso 0.5 1 calc R U P C -1
H37E H 0.7332 1.0089 0.2653 0.099 Uiso 0.5 1 calc R U P C -1
H37F H 0.8914 1.0528 0.2567 0.099 Uiso 0.5 1 calc R U P C -1
C42 C 0.45407(15) 0.7500 0.04105(9) 0.0369(3) Uani 1 2 d S T P C .
H42A H 0.3910 0.6972 0.0454 0.044 Uiso 0.5 1 calc R U P . .
H42B H 0.3910 0.8028 0.0454 0.044 Uiso 0.5 1 calc R U P . .
C43 C 0.48464(15) 0.7500 -0.05357(9) 0.0374(3) Uani 1 2 d S T P . .
H43A H 0.5461 0.6969 -0.0595 0.045 Uiso 0.5 1 calc R U P C .
H43B H 0.5461 0.8031 -0.0595 0.045 Uiso 0.5 1 calc R U P . .
C44 C 0.33260(17) 0.7500 -0.13100(10) 0.0382(3) Uani 1 2 d S T P C .
H44A H 0.2713 0.6970 -0.1245 0.046 Uiso 0.5 1 calc R U P . .
H44B H 0.2713 0.8030 -0.1245 0.046 Uiso 0.5 1 calc R U P . .
C45 C 0.3584(2) 0.7500 -0.22662(11) 0.0584(4) Uani 1 2 d S T P . .
H45A H 0.2596 0.7383 -0.2737 0.088 Uiso 0.5 1 calc R U P C .
H45B H 0.4338 0.7038 -0.2297 0.088 Uiso 0.5 1 calc R U P . .
H45C H 0.3986 0.8078 -0.2386 0.088 Uiso 0.5 1 calc R U P . .
C46 C 0.54027(19) 0.76794(13) 0.21060(11) 0.0324(7) Uani 0.5 1 d . . P C -1
H46A H 0.4483 0.7302 0.2072 0.039 Uiso 0.5 1 calc R U P C -1
H46B H 0.5066 0.8305 0.2093 0.039 Uiso 0.5 1 calc R U P C -1
C47 C 0.66401(16) 0.7500 0.30370(10) 0.0441(4) Uani 1 2 d S T P . .
H47A H 0.7159 0.8067 0.3269 0.053 Uiso 0.5 1 calc R U P C -1
H47B H 0.7439 0.7102 0.2913 0.053 Uiso 0.5 1 calc R U P C -1
C48 C 0.6033(2) 0.70759(14) 0.38358(13) 0.0383(4) Uani 0.5 1 d . . P C -1
H48A H 0.5663 0.6466 0.3659 0.046 Uiso 0.5 1 calc R U P C -1
H48B H 0.6894 0.7045 0.4419 0.046 Uiso 0.5 1 calc R U P C -1
C49 C 0.4724(2) 0.7624(9) 0.39951(15) 0.054(2) Uani 0.5 1 d . . P C -1
H49A H 0.3802 0.7561 0.3460 0.080 Uiso 0.5 1 calc R U P C -1
H49B H 0.5038 0.8247 0.4068 0.080 Uiso 0.5 1 calc R U P C -1
H49C H 0.4479 0.7419 0.4561 0.080 Uiso 0.5 1 calc R U P C -1
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'
F F 0.0727 0.0534 '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'
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
C7 N2 C8 123.32(8) . .
C7 N2 H2N 121.7(7) . .
C8 N2 H2N 114.9(7) . .
C11 N1 C28 123.5(2) . .
C11 N1 H1N 119.2(14) . .
C28 N1 H1N 117.1(15) . .
O1 C11 N1 125.93(18) . .
O1 C11 C2 114.90(18) . .
N1 C11 C2 119.11(16) . .
C6 N5 C2 119.15(10) . .
C6 C1 C2 119.15(10) . .
C6 C1 H1 120.4 . .
C2 C1 H1 120.4 . .
C1 C2 C3 121.54(11) . .
N5 C2 C3 121.54(11) . .
N5 C2 C11 111.47(12) . .
C3 C2 C11 126.97(14) . .
C1 C2 H2A 119.2 . .
C3 C2 H2A 119.2 . .
C4 C3 C2 119.03(11) . .
C4 C3 H3 120.5 . .
C2 C3 H3 120.5 . .
C3 C4 C5 119.48(11) . .
C3 C4 H4 120.3 . .
C5 C4 H4 120.3 . .
C4 C5 C6 119.15(10) . .
C4 C5 H5 120.4 . .
C6 C5 H5 120.4 . .
C1 C6 C5 121.63(10) . .
N5 C6 C5 121.63(10) . .
C1 C6 C7 119.71(9) . .
N5 C6 C7 119.71(9) . .
C5 C6 C7 118.66(9) . .
O2 C7 N2 124.15(9) . .
O2 C7 C6 120.17(9) . .
N2 C7 C6 115.66(8) . .
C9 C8 C8 119.44(6) . 4_575
C9 C8 N2 120.99(9) . .
C8 C8 N2 119.52(5) 4_575 .
C10 C9 C8 120.28(10) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
C9 C10 C10 120.27(6) . 4_575
C9 C10 H10 119.9 . .
C10 C10 H10 119.9 4_575 .
C33 C28 N1 118.3(7) . .
C33 C28 C29 117.3(8) . .
N1 C28 C29 124.3(4) . .
C32 C33 C28 122.9(8) . .
C32 C33 H33 118.6 . .
C28 C33 H33 118.6 . .
C31 C32 C33 119.4(4) . .
C31 C32 H32 120.3 . .
C33 C32 H32 120.3 . .
C30 C31 C32 119.0(6) . .
C30 C31 H31 120.5 . .
C32 C31 H31 120.5 . .
C31 C30 C29 121.6(7) . .
C31 C30 H30 119.2 . .
C29 C30 H30 119.2 . .
C28 C29 C30 119.7(4) . .
C28 C29 H29 120.2 . .
C30 C29 H29 120.2 . .
C34A N7 C42 113.8(4) . .
C34A N7 C46 117.8(3) . .
C42 N7 C46 106.25(10) . .
C34A N7 C34B 106.35(12) . .
C42 N7 C34B 109.0(4) . .
C46 N7 C34B 102.9(3) . .
N7 C34A C35A 107.4(5) . .
N7 C34A H34A 110.2 . .
C35A C34A H34A 110.2 . .
N7 C34A H34B 110.2 . .
C35A C34A H34B 110.2 . .
H34A C34A H34B 108.5 . .
C35B C34B N7 124.8(5) . .
C35B C34B H34C 106.1 . .
N7 C34B H34C 106.1 . .
C35B C34B H34D 106.1 . .
N7 C34B H34D 106.1 . .
H34C C34B H34D 106.3 . .
C36A C35A C34A 109.8(4) . .
C36A C35A H35A 109.7 . .
C34A C35A H35A 109.7 . .
C36A C35A H35B 109.7 . .
C34A C35A H35B 109.7 . .
H35A C35A H35B 108.2 . .
C37A C36A C35A 115.1(4) . .
C37A C36A H36A 108.5 . .
C35A C36A H36A 108.5 . .
C37A C36A H36B 108.5 . .
C35A C36A H36B 108.5 . .
H36A C36A H36B 107.5 . .
C34B C35B C36B 112.3(4) . .
C34B C35B H35C 109.1 . .
C36B C35B H35C 109.1 . .
C34B C35B H35D 109.1 . .
C36B C35B H35D 109.1 . .
H35C C35B H35D 107.9 . .
C35B C36B C37B 111.6(4) . .
C35B C36B H36C 109.3 . .
C37B C36B H36C 109.3 . .
C35B C36B H36D 109.3 . .
C37B C36B H36D 109.3 . .
H36C C36B H36D 108.0 . .
C36A C37A H37A 109.5 . .
C36A C37A H37B 109.5 . .
H37A C37A H37B 109.5 . .
C36A C37A H37C 109.5 . .
H37A C37A H37C 109.5 . .
H37B C37A H37C 109.5 . .
C36B C37B H37D 109.5 . .
C36B C37B H37E 109.5 . .
H37D C37B H37E 109.5 . .
C36B C37B H37F 109.5 . .
H37D C37B H37F 109.5 . .
H37E C37B H37F 109.5 . .
C43 C42 N7 115.59(10) . .
C43 C42 H42A 108.4 . .
N7 C42 H42A 108.4 . .
C43 C42 H42B 108.4 . .
N7 C42 H42B 108.4 . .
H42A C42 H42B 107.4 . .
C42 C43 C44 110.73(11) . .
C42 C43 H43A 109.5 . .
C44 C43 H43A 109.5 . .
C42 C43 H43B 109.5 . .
C44 C43 H43B 109.5 . .
H43A C43 H43B 108.1 . .
C45 C44 C43 112.28(13) . .
C45 C44 H44A 109.1 . .
C43 C44 H44A 109.1 . .
C45 C44 H44B 109.1 . .
C43 C44 H44B 109.1 . .
H44A C44 H44B 107.9 . .
C44 C45 H45A 109.5 . .
C44 C45 H45B 109.5 . .
H45A C45 H45B 109.5 . .
C44 C45 H45C 109.5 . .
H45A C45 H45C 109.5 . .
H45B C45 H45C 109.5 . .
N7 C46 C47 113.56(12) . .
N7 C46 H46A 108.9 . .
C47 C46 H46A 108.9 . .
N7 C46 H46B 108.9 . .
C47 C46 H46B 108.9 . .
H46A C46 H46B 107.7 . .
C46 C47 C48 116.16(12) . .
C46 C47 H47A 108.2 . .
C48 C47 H47A 108.2 . .
C46 C47 H47B 108.2 . .
C48 C47 H47B 108.2 . .
H47A C47 H47B 107.4 . .
C49 C48 C47 110.0(3) . .
C49 C48 H48A 109.7 . .
C47 C48 H48A 109.7 . .
C49 C48 H48B 109.7 . .
C47 C48 H48B 109.7 . .
H48A C48 H48B 108.2 . .
C48 C49 H49A 109.5 . .
C48 C49 H49B 109.5 . .
H49A C49 H49B 109.5 . .
C48 C49 H49C 109.5 . .
H49A C49 H49C 109.5 . .
H49B C49 H49C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C7 1.2295(12) .
N2 C7 1.3540(13) .
N2 C8 1.4190(11) .
N2 H2N 0.914(12) .
O1 C11 1.221(2) .
N1 C11 1.352(3) .
N1 C28 1.390(7) .
N1 H1N 0.91(2) .
C11 C2 1.433(2) .
N5 C6 1.3360(14) .
N5 C2 1.3648(17) .
C1 C6 1.3360(14) .
C1 C2 1.3648(17) .
C1 H1 0.9500 .
C2 C3 1.3849(17) .
C2 H2A 0.9500 .
C3 C4 1.3788(17) .
C3 H3 0.9500 .
C4 C5 1.3826(16) .
C4 H4 0.9500 .
C5 C6 1.3933(15) .
C5 H5 0.9500 .
C6 C7 1.5023(14) .
C8 C9 1.3967(13) .
C8 C8 1.4037(19) 4_575
C9 C10 1.3820(14) .
C9 H9 0.9500 .
C10 C10 1.383(2) 4_575
C10 H10 0.9500 .
C28 C33 1.385(4) .
C28 C29 1.392(7) .
C33 C32 1.379(7) .
C33 H33 0.9500 .
C32 C31 1.376(6) .
C32 H32 0.9500 .
C31 C30 1.372(5) .
C31 H31 0.9500 .
C30 C29 1.399(6) .
C30 H30 0.9500 .
C29 H29 0.9500 .
N7 C34A 1.436(11) .
N7 C42 1.5200(16) .
N7 C46 1.5382(18) .
N7 C34B 1.589(11) .
C34A C35A 1.596(9) .
C34A H34A 0.9900 .
C34A H34B 0.9900 .
C34B C35B 1.451(11) .
C34B H34C 0.9900 .
C34B H34D 0.9900 .
C35A C36A 1.530(4) .
C35A H35A 0.9900 .
C35A H35B 0.9900 .
C36A C37A 1.475(9) .
C36A H36A 0.9900 .
C36A H36B 0.9900 .
C35B C36B 1.518(4) .
C35B H35C 0.9900 .
C35B H35D 0.9900 .
C36B C37B 1.533(9) .
C36B H36C 0.9900 .
C36B H36D 0.9900 .
C37A H37A 0.9800 .
C37A H37B 0.9800 .
C37A H37C 0.9800 .
C37B H37D 0.9800 .
C37B H37E 0.9800 .
C37B H37F 0.9800 .
C42 C43 1.5113(18) .
C42 H42A 0.9900 .
C42 H42B 0.9900 .
C43 C44 1.5203(19) .
C43 H43A 0.9900 .
C43 H43B 0.9900 .
C44 C45 1.508(2) .
C44 H44A 0.9900 .
C44 H44B 0.9900 .
C45 H45A 0.9800 .
C45 H45B 0.9800 .
C45 H45C 0.9800 .
C46 C47 1.541(2) .
C46 H46A 0.9900 .
C46 H46B 0.9900 .
C47 C48 1.577(2) .
C47 H47A 0.9900 .
C47 H47B 0.9900 .
C48 C49 1.506(8) .
C48 H48A 0.9900 .
C48 H48B 0.9900 .
C49 H49A 0.9800 .
C49 H49B 0.9800 .
C49 H49C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2N F1 0.914(12) 1.772(12) 2.6617(10) 163.9(11)
N1 H1N F1 0.91(2) 1.96(2) 2.8413(16) 162(2)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C28 N1 C11 O1 -0.6(4) . .
C28 N1 C11 C2 176.3(3) . .
C6 C1 C2 C3 0.01(19) . .
C6 N5 C2 C3 0.01(19) . .
C6 N5 C2 C11 178.44(12) . .
O1 C11 C2 N5 -178.47(17) . .
N1 C11 C2 N5 4.3(2) . .
O1 C11 C2 C3 -0.1(3) . .
N1 C11 C2 C3 -177.38(15) . .
C1 C2 C3 C4 -0.8(2) . .
N5 C2 C3 C4 -0.8(2) . .
C11 C2 C3 C4 -178.99(16) . .
C2 C3 C4 C5 1.2(2) . .
C3 C4 C5 C6 -0.91(19) . .
C2 C1 C6 C5 0.35(16) . .
C2 C1 C6 C7 -179.57(10) . .
C2 N5 C6 C5 0.35(16) . .
C2 N5 C6 C7 -179.57(10) . .
C4 C5 C6 C1 0.11(16) . .
C4 C5 C6 N5 0.11(16) . .
C4 C5 C6 C7 -179.97(10) . .
C8 N2 C7 O2 -3.88(14) . .
C8 N2 C7 C6 177.60(8) . .
C1 C6 C7 O2 175.59(9) . .
N5 C6 C7 O2 175.59(9) . .
C5 C6 C7 O2 -4.34(14) . .
C1 C6 C7 N2 -5.83(13) . .
N5 C6 C7 N2 -5.83(13) . .
C5 C6 C7 N2 174.25(9) . .
C7 N2 C8 C9 -41.56(12) . .
C7 N2 C8 C8 141.07(7) . 4_575
C8 C8 C9 C10 -1.08(10) 4_575 .
N2 C8 C9 C10 -178.45(8) . .
C8 C9 C10 C10 1.09(11) . 4_575
C11 N1 C28 C33 -154.1(4) . .
C11 N1 C28 C29 28.3(6) . .
N1 C28 C33 C32 -178.7(3) . .
C29 C28 C33 C32 -0.9(9) . .
C28 C33 C32 C31 -1.5(8) . .
C33 C32 C31 C30 3.0(9) . .
C32 C31 C30 C29 -2.2(10) . .
C33 C28 C29 C30 1.7(7) . .
N1 C28 C29 C30 179.3(4) . .
C31 C30 C29 C28 -0.2(8) . .
C42 N7 C34A C35A -60.4(6) . .
C46 N7 C34A C35A 64.9(7) . .
C34B N7 C34A C35A 179.6(7) . .
C34A N7 C34B C35B 171.1(10) . .
C42 N7 C34B C35B 48.0(8) . .
C46 N7 C34B C35B -64.5(8) . .
N7 C34A C35A C36A -177.5(5) . .
C34A C35A C36A C37A 74.1(6) . .
N7 C34B C35B C36B 161.0(5) . .
C34B C35B C36B C37B -72.6(6) . .
C34A N7 C42 C43 -59.3(3) . .
C46 N7 C42 C43 169.43(8) . .
C34B N7 C42 C43 59.2(3) . .
N7 C42 C43 C44 180.000(0) . .
C42 C43 C44 C45 180.000(0) . .
C34A N7 C46 C47 38.2(4) . .
C42 N7 C46 C47 167.15(9) . .
C34B N7 C46 C47 -78.4(4) . .
N7 C46 C47 C48 -142.31(13) . .
C46 C47 C48 C49 -53.6(3) . .
