#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/54/2225494.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2225494
loop_
_publ_author_name
'Meskini, Ihssan'
'Daoudi, Maria'
'Daran, Jean-Claude'
'Zouihri, Hafid'
'Kerbal, Abdelali'
_publ_section_title
;
 Diethyl 2-{(dibenzylamino)[4-(trifluoromethyl)phenyl]methyl}malonate
;
_journal_coeditor_code           CV2702
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o961
_journal_page_last               o962
_journal_paper_doi               10.1107/S1600536810010512
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C29 H30 F3 N O4'
_chemical_formula_moiety         'C29 H30 F3 N O4'
_chemical_formula_sum            'C29 H30 F3 N O4'
_chemical_formula_weight         513.54
_chemical_melting_point          375
_chemical_name_systematic
;
Diethyl 2-{(dibenzylamino)[4-(trifluoromethyl)phenyl]methyl}malonate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.8260(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.4131(3)
_cell_length_b                   23.6608(5)
_cell_length_c                   17.3769(3)
_cell_measurement_pressure       101
_cell_measurement_reflns_used    5382
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      2.5
_cell_volume                     5475.72(19)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            74220
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.409
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     709
_refine_ls_number_reflns         10790
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0600
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0764P)²+3.8750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1836
_reflns_number_gt                6912
_reflns_number_total             10790
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2702.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225494
_cod_database_fobs_code          2225494
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.21351(13) 0.55799(8) 0.47972(11) 0.0377(5) Uani d . 1 . .
O O12 0.13397(17) 0.71894(10) 0.37972(14) 0.0757(6) Uani d . 1 . .
O O13 0.20149(13) 0.68514(8) 0.56473(11) 0.0531(5) Uani d . 1 . .
O O14 0.08360(14) 0.62505(9) 0.59701(11) 0.0610(5) Uani d . 1 . .
F F11 0.0021(2) 0.5779(2) 0.07329(13) 0.206(2) Uani d . 1 . .
F F12 0.0673(3) 0.49891(18) 0.09034(15) 0.1527(13) Uani d . 1 . .
F F13 0.1539(2) 0.56371(14) 0.05959(12) 0.1232(10) Uani d . 1 . .
C C11 0.18374(16) 0.60674(11) 0.42886(13) 0.0393(5) Uani d . 1 . .
H H11 0.2426 0.6315 0.4314 0.047 Uiso calc R 1 . .
C C12 0.13542(17) 0.51487(11) 0.48334(14) 0.0420(6) Uani d . 1 . .
H H12A 0.1268 0.4938 0.4351 0.050 Uiso calc R 1 . .
H H12B 0.0722 0.5332 0.4896 0.050 Uiso calc R 1 . .
C C13 0.30752(17) 0.53227(11) 0.46200(15) 0.0420(6) Uani d . 1 . .
H H13A 0.3020 0.5241 0.4069 0.050 Uiso calc R 1 . .
H H13B 0.3170 0.4967 0.4895 0.050 Uiso calc R 1 . .
C C14 0.10159(17) 0.64086(11) 0.46267(15) 0.0430(6) Uani d . 1 . .
H H14 0.0388 0.6194 0.4535 0.052 Uiso calc R 1 . .
C C111 0.15593(17) 0.59254(11) 0.34376(14) 0.0421(6) Uani d . 1 . .
C C112 0.06123(18) 0.57289(12) 0.31431(15) 0.0500(7) Uani d . 1 . .
H H112 0.0125 0.5679 0.3476 0.060 Uiso calc R 1 . .
C C113 0.0385(2) 0.56065(14) 0.23677(17) 0.0610(8) Uani d . 1 . .
H H113 -0.0254 0.5479 0.2181 0.073 Uiso calc R 1 . .
C C114 0.1102(2) 0.56730(14) 0.18657(16) 0.0592(8) Uani d . 1 . .
C C115 0.2050(2) 0.58634(14) 0.21465(16) 0.0585(8) Uani d . 1 . .
H H115 0.2537 0.5907 0.1813 0.070 Uiso calc R 1 . .
C C116 0.22705(19) 0.59887(12) 0.29234(15) 0.0491(6) Uani d . 1 . .
H H116 0.2909 0.6118 0.3107 0.059 Uiso calc R 1 . .
C C117 0.0831(3) 0.5552(2) 0.1027(2) 0.0897(13) Uani d . 1 . .
C C121 0.16261(17) 0.47463(11) 0.54984(14) 0.0434(6) Uani d . 1 . .
C C122 0.15670(18) 0.41678(12) 0.53886(16) 0.0490(6) Uani d . 1 . .
H H122 0.1359 0.4024 0.4898 0.059 Uiso calc R 1 . .
C C123 0.18166(19) 0.37990(13) 0.60070(19) 0.0573(8) Uani d . 1 . .
H H123 0.1769 0.3411 0.5928 0.069 Uiso calc R 1 . .
C C124 0.2131(2) 0.40070(16) 0.67316(19) 0.0644(9) Uani d . 1 . .
H H124 0.2303 0.3761 0.7143 0.077 Uiso calc R 1 . .
C C125 0.2192(2) 0.45806(15) 0.68468(17) 0.0618(8) Uani d . 1 . .
H H125 0.2406 0.4722 0.7338 0.074 Uiso calc R 1 . .
C C126 0.1940(2) 0.49465(13) 0.62428(16) 0.0530(7) Uani d . 1 . .
H H126 0.1979 0.5334 0.6331 0.064 Uiso calc R 1 . .
C C131 0.39848(16) 0.56895(11) 0.48345(14) 0.0387(5) Uani d . 1 . .
C C132 0.47653(18) 0.56848(12) 0.43764(16) 0.0495(6) Uani d . 1 . .
H H132 0.4706 0.5472 0.3924 0.059 Uiso calc R 1 . .
C C133 0.56274(19) 0.59933(15) 0.45864(18) 0.0619(8) Uani d . 1 . .
H H133 0.6148 0.5982 0.4278 0.074 Uiso calc R 1 . .
C C134 0.5725(2) 0.63169(14) 0.52458(19) 0.0622(8) Uani d . 1 . .
H H134 0.6306 0.6526 0.5383 0.075 Uiso calc R 1 . .
C C135 0.4952(2) 0.63286(13) 0.57037(17) 0.0573(7) Uani d . 1 . .
H H135 0.5011 0.6547 0.6152 0.069 Uiso calc R 1 . .
C C136 0.40904(18) 0.60163(12) 0.54986(15) 0.0476(6) Uani d . 1 . .
H H136 0.3575 0.6026 0.5812 0.057 Uiso calc R 1 . .
C C141 0.0843(2) 0.69809(13) 0.42430(18) 0.0564(7) Uani d . 1 A .
O O11 0.00554(18) 0.72241(10) 0.45047(17) 0.0879(8) Uani d D 1 . .
C C143 -0.0206(18) 0.7772(5) 0.4092(9) 0.099(5) Uani d PD 0.47 A 1
H H14A 0.0313 0.7881 0.3776 0.119 Uiso calc PR 0.47 A 1
H H14B -0.0840 0.7742 0.3762 0.119 Uiso calc PR 0.47 A 1
C C144 -0.0277(16) 0.8177(5) 0.4702(9) 0.217(11) Uani d PD 0.47 A 1
H H14C -0.0817 0.8073 0.4990 0.326 Uiso calc PR 0.47 A 1
H H14D -0.0403 0.8546 0.4481 0.326 Uiso calc PR 0.47 A 1
H H14E 0.0342 0.8182 0.5042 0.326 Uiso calc PR 0.47 A 1
C C14B -0.0790(11) 0.7854(5) 0.3714(8) 0.174(7) Uani d PD 0.53 A 2
H H14F -0.0454 0.7706 0.3300 0.261 Uiso calc PR 0.53 A 2
H H14G -0.0998 0.8236 0.3597 0.261 Uiso calc PR 0.53 A 2
H H14H -0.1368 0.7626 0.3773 0.261 Uiso calc PR 0.53 A 2
C C14A -0.0121(16) 0.7845(6) 0.4419(9) 0.113(6) Uani d PD 0.53 A 2
H H14I -0.0432 0.7999 0.4849 0.136 Uiso calc PR 0.53 A 2
H H14J 0.0496 0.8048 0.4368 0.136 Uiso calc PR 0.53 A 2
C C142 0.12649(18) 0.64860(12) 0.54960(16) 0.0463(6) Uani d . 1 . .
C C145 0.2325(2) 0.69825(15) 0.64581(18) 0.0685(9) Uani d . 1 . .
H H14K 0.3027 0.7090 0.6525 0.082 Uiso calc R 1 . .
H H14L 0.2249 0.6650 0.6772 0.082 Uiso calc R 1 . .
C C146 0.1703(3) 0.7456(2) 0.6722(3) 0.1027(14) Uani d . 1 . .
H H14M 0.1750 0.7779 0.6394 0.154 Uiso calc R 1 . .
H H14N 0.1945 0.7554 0.7248 0.154 Uiso calc R 1 . .
H H14O 0.1015 0.7338 0.6695 0.154 Uiso calc R 1 . .
N N2 0.38330(14) 0.41631(8) 0.17015(11) 0.0379(4) Uani d . 1 . .
O O22 0.66181(15) 0.44204(10) 0.08333(13) 0.0670(6) Uani d . 1 . .
O O23 0.54397(17) 0.32714(8) 0.10776(12) 0.0624(5) Uani d . 1 . .
O O24 0.54353(15) 0.31656(8) 0.23671(12) 0.0604(5) Uani d . 1 . .
F F21 0.4756(3) 0.71223(9) 0.11140(17) 0.1370(11) Uani d . 1 . .
F F22 0.56193(16) 0.70396(8) 0.22086(16) 0.1008(8) Uani d . 1 . .
F F23 0.40388(17) 0.69796(8) 0.21172(16) 0.1031(8) Uani d . 1 . .
C C21 0.47579(17) 0.44015(10) 0.14446(13) 0.0353(5) Uani d . 1 . .
H H21 0.4729 0.4318 0.0890 0.042 Uiso calc R 1 . .
C C22 0.29368(18) 0.43168(11) 0.11700(14) 0.0431(6) Uani d . 1 . .
H H22A 0.2941 0.4722 0.1082 0.052 Uiso calc R 1 . .
H H22B 0.2343 0.4228 0.1415 0.052 Uiso calc R 1 . .
C C23 0.36784(19) 0.42964(11) 0.25048(14) 0.0438(6) Uani d . 1 . .
H H23A 0.3486 0.4690 0.2539 0.053 Uiso calc R 1 . .
H H23B 0.4302 0.4241 0.2840 0.053 Uiso calc R 1 . .
C C24 0.56778(17) 0.40876(10) 0.18446(14) 0.0396(5) Uani d . 1 . .
H H24 0.5791 0.4205 0.2389 0.048 Uiso calc R 1 . .
C C211 0.48513(17) 0.50390(10) 0.15241(13) 0.0358(5) Uani d . 1 . .
C C212 0.51929(18) 0.53005(11) 0.22226(14) 0.0423(6) Uani d . 1 . .
H H212 0.5422 0.5081 0.2652 0.051 Uiso calc R 1 . .
C C213 0.5196(2) 0.58816(11) 0.22867(16) 0.0485(6) Uani d . 1 . .
H H213 0.5419 0.6051 0.2759 0.058 Uiso calc R 1 . .
C C214 0.4870(2) 0.62105(11) 0.16538(16) 0.0482(6) Uani d . 1 . .
C C215 0.4547(2) 0.59608(11) 0.09484(16) 0.0496(6) Uani d . 1 . .
H H215 0.4337 0.6183 0.0518 0.060 Uiso calc R 1 . .
C C216 0.45416(18) 0.53773(10) 0.08905(14) 0.0413(6) Uani d . 1 . .
H H216 0.4325 0.5209 0.0416 0.050 Uiso calc R 1 . .
C C217 0.4827(3) 0.68374(13) 0.1760(2) 0.0680(9) Uani d . 1 . .
C C221 0.28691(18) 0.40196(12) 0.04024(14) 0.0457(6) Uani d . 1 . .
C C222 0.2986(3) 0.34475(14) 0.03616(19) 0.0717(9) Uani d . 1 . .
H H222 0.3143 0.3239 0.0813 0.086 Uiso calc R 1 . .
C C223 0.2871(3) 0.31745(17) -0.0360(2) 0.0963(13) Uani d . 1 . .
H H223 0.2951 0.2785 -0.0389 0.116 Uiso calc R 1 . .
C C224 0.2639(3) 0.34860(19) -0.1022(2) 0.0919(12) Uani d . 1 . .
H H224 0.2568 0.3307 -0.1501 0.110 Uiso calc R 1 . .
C C225 0.2514(3) 0.40534(18) -0.09839(19) 0.0822(11) Uani d . 1 . .
H H225 0.2348 0.4261 -0.1436 0.099 Uiso calc R 1 . .
C C226 0.2631(2) 0.43214(14) -0.02777(16) 0.0599(8) Uani d . 1 . .
H H226 0.2549 0.4711 -0.0256 0.072 Uiso calc R 1 . .
C C231 0.28758(19) 0.39275(13) 0.27726(14) 0.0494(7) Uani d . 1 . .
C C232 0.2990(2) 0.33483(15) 0.2789(2) 0.0697(9) Uani d . 1 . .
H H232 0.3558 0.3183 0.2625 0.084 Uiso calc R 1 . .
C C233 0.2253(3) 0.30143(19) 0.3049(3) 0.1002(14) Uani d . 1 . .
H H233 0.2329 0.2624 0.3064 0.120 Uiso calc R 1 . .
C C234 0.1405(3) 0.3259(3) 0.3289(2) 0.1038(16) Uani d . 1 . .
H H234 0.0913 0.3032 0.3467 0.125 Uiso calc R 1 . .
C C235 0.1292(3) 0.3825(2) 0.3265(2) 0.0914(13) Uani d . 1 . .
H H235 0.0718 0.3989 0.3420 0.110 Uiso calc R 1 . .
C C236 0.2017(2) 0.41593(16) 0.30118(17) 0.0656(9) Uani d . 1 . .
H H236 0.1933 0.4549 0.3000 0.079 Uiso calc R 1 . .
C C242 0.55040(19) 0.34538(11) 0.18100(16) 0.0470(6) Uani d . 1 . .
C C241 0.66075(19) 0.42246(12) 0.14585(17) 0.0492(6) Uani d . 1 B .
O O21 0.74317(16) 0.40944(13) 0.19179(15) 0.0946(9) Uani d D 1 . .
C C243 0.8360(4) 0.4181(6) 0.1506(4) 0.090(3) Uani d PD 0.64 B 3
H H24A 0.8342 0.3933 0.1061 0.109 Uiso calc PR 0.64 B 3
H H24B 0.8398 0.4569 0.1332 0.109 Uiso calc PR 0.64 B 3
C C244 0.9203(4) 0.4050(5) 0.2061(4) 0.109(3) Uani d PD 0.64 B 3
H H24C 0.9181 0.4279 0.2515 0.163 Uiso calc PR 0.64 B 3
H H24D 0.9812 0.4125 0.1841 0.163 Uiso calc PR 0.64 B 3
H H24E 0.9180 0.3658 0.2201 0.163 Uiso calc PR 0.64 B 3
C C24A 0.8544(10) 0.4324(5) 0.1860(10) 0.128(8) Uani d PD 0.36 B 4
H H24F 0.8582 0.4645 0.1516 0.154 Uiso calc PR 0.36 B 4
H H24G 0.8952 0.4379 0.2354 0.154 Uiso calc PR 0.36 B 4
C C24B 0.8650(19) 0.3778(6) 0.1505(12) 0.146(8) Uani d PD 0.36 B 4
H H24H 0.8623 0.3486 0.1887 0.219 Uiso calc PR 0.36 B 4
H H24I 0.9283 0.3760 0.1300 0.219 Uiso calc PR 0.36 B 4
H H24J 0.8115 0.3724 0.1094 0.219 Uiso calc PR 0.36 B 4
C C245 0.5254(3) 0.26672(13) 0.0932(2) 0.0752(9) Uani d . 1 . .
H H24K 0.4916 0.2507 0.1346 0.090 Uiso calc R 1 . .
H H24L 0.4822 0.2618 0.0448 0.090 Uiso calc R 1 . .
C C246 0.6197(3) 0.23760(18) 0.0893(3) 0.1093(16) Uani d . 1 . .
H H24M 0.6521 0.2529 0.0475 0.164 Uiso calc R 1 . .
H H24N 0.6071 0.1980 0.0804 0.164 Uiso calc R 1 . .
H H24O 0.6623 0.2425 0.1372 0.164 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 N1 C12 . . 110.9(2) ?
C13 N1 C11 . . 112.11(17) ?
C12 N1 C11 . . 115.09(18) ?
C142 O13 C145 . . 116.9(2) ?
N1 C11 C111 . . 115.3(2) ?
N1 C11 C14 . . 109.64(18) ?
C111 C11 C14 . . 112.57(19) ?
N1 C11 H11 . . 106.2 ?
C111 C11 H11 . . 106.2 ?
C14 C11 H11 . . 106.2 ?
N1 C12 C121 . . 111.26(19) ?
N1 C12 H12A . . 109.4 ?
C121 C12 H12A . . 109.4 ?
N1 C12 H12B . . 109.4 ?
C121 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
N1 C13 C131 . . 113.6(2) ?
N1 C13 H13A . . 108.8 ?
C131 C13 H13A . . 108.8 ?
N1 C13 H13B . . 108.8 ?
C131 C13 H13B . . 108.8 ?
H13A C13 H13B . . 107.7 ?
C141 C14 C142 . . 109.5(2) ?
C141 C14 C11 . . 112.3(2) ?
C142 C14 C11 . . 111.1(2) ?
C141 C14 H14 . . 107.9 ?
C142 C14 H14 . . 107.9 ?
C11 C14 H14 . . 107.9 ?
C116 C111 C112 . . 117.7(2) ?
C116 C111 C11 . . 119.6(2) ?
C112 C111 C11 . . 122.7(2) ?
C113 C112 C111 . . 121.1(2) ?
C113 C112 H112 . . 119.5 ?
C111 C112 H112 . . 119.5 ?
C112 C113 C114 . . 120.3(3) ?
C112 C113 H113 . . 119.9 ?
C114 C113 H113 . . 119.9 ?
C115 C114 C113 . . 119.6(3) ?
C115 C114 C117 . . 121.1(3) ?
C113 C114 C117 . . 119.2(3) ?
C116 C115 C114 . . 119.8(3) ?
C116 C115 H115 . . 120.1 ?
C114 C115 H115 . . 120.1 ?
C115 C116 C111 . . 121.5(2) ?
C115 C116 H116 . . 119.3 ?
C111 C116 H116 . . 119.3 ?
F11 C117 F13 . . 110.7(4) ?
F11 C117 F12 . . 104.0(4) ?
F13 C117 F12 . . 99.9(3) ?
F11 C117 C114 . . 114.4(3) ?
F13 C117 C114 . . 115.2(3) ?
F12 C117 C114 . . 111.1(4) ?
C122 C121 C126 . . 118.0(2) ?
C122 C121 C12 . . 121.0(2) ?
C126 C121 C12 . . 121.0(2) ?
C121 C122 C123 . . 120.6(3) ?
C121 C122 H122 . . 119.7 ?
C123 C122 H122 . . 119.7 ?
C124 C123 C122 . . 120.2(3) ?
C124 C123 H123 . . 119.9 ?
C122 C123 H123 . . 119.9 ?
C123 C124 C125 . . 119.7(3) ?
C123 C124 H124 . . 120.2 ?
C125 C124 H124 . . 120.2 ?
C126 C125 C124 . . 120.5(3) ?
C126 C125 H125 . . 119.8 ?
C124 C125 H125 . . 119.8 ?
C125 C126 C121 . . 121.0(3) ?
C125 C126 H126 . . 119.5 ?
C121 C126 H126 . . 119.5 ?
C136 C131 C132 . . 118.3(2) ?
C136 C131 C13 . . 121.9(2) ?
C132 C131 C13 . . 119.8(2) ?
C133 C132 C131 . . 120.6(3) ?
C133 C132 H132 . . 119.7 ?
C131 C132 H132 . . 119.7 ?
C134 C133 C132 . . 120.7(3) ?
C134 C133 H133 . . 119.7 ?
C132 C133 H133 . . 119.7 ?
C133 C134 C135 . . 119.3(3) ?
C133 C134 H134 . . 120.3 ?
C135 C134 H134 . . 120.3 ?
C134 C135 C136 . . 120.2(3) ?
C134 C135 H135 . . 119.9 ?
C136 C135 H135 . . 119.9 ?
C135 C136 C131 . . 120.9(2) ?
C135 C136 H136 . . 119.5 ?
C131 C136 H136 . . 119.5 ?
O12 C141 O11 . . 125.0(3) ?
O12 C141 C14 . . 126.2(3) ?
O11 C141 C14 . . 108.8(3) ?
C141 O11 C14A . . 121.0(9) ?
C141 O11 C143 . . 111.1(8) ?
C14A O11 C143 . . 22.8(9) ?
C144 C143 O11 . . 104.8(11) ?
C144 C143 H14A . . 110.8 ?
O11 C143 H14A . . 110.8 ?
C144 C143 H14B . . 110.8 ?
O11 C143 H14B . . 110.8 ?
H14A C143 H14B . . 108.9 ?
C14A C14B H14F . . 109.5 ?
C14A C14B H14G . . 109.5 ?
H14F C14B H14G . . 109.5 ?
C14A C14B H14H . . 109.5 ?
H14F C14B H14H . . 109.5 ?
H14G C14B H14H . . 109.5 ?
C14B C14A O11 . . 100.2(11) ?
C14B C14A H14I . . 111.7 ?
O11 C14A H14I . . 111.7 ?
C14B C14A H14J . . 111.7 ?
O11 C14A H14J . . 111.7 ?
H14I C14A H14J . . 109.5 ?
O14 C142 O13 . . 125.5(3) ?
O14 C142 C14 . . 124.2(2) ?
O13 C142 C14 . . 110.3(2) ?
O13 C145 C146 . . 110.5(3) ?
O13 C145 H14K . . 109.5 ?
C146 C145 H14K . . 109.5 ?
O13 C145 H14L . . 109.5 ?
C146 C145 H14L . . 109.5 ?
H14K C145 H14L . . 108.1 ?
C145 C146 H14M . . 109.5 ?
C145 C146 H14N . . 109.5 ?
H14M C146 H14N . . 109.5 ?
C145 C146 H14O . . 109.5 ?
H14M C146 H14O . . 109.5 ?
H14N C146 H14O . . 109.5 ?
C23 N2 C22 . . 110.25(19) ?
C23 N2 C21 . . 115.01(18) ?
C22 N2 C21 . . 111.59(18) ?
C242 O23 C245 . . 117.9(2) ?
N2 C21 C211 . . 114.48(18) ?
N2 C21 C24 . . 109.68(18) ?
C211 C21 C24 . . 112.74(19) ?
N2 C21 H21 . . 106.5 ?
C211 C21 H21 . . 106.5 ?
C24 C21 H21 . . 106.5 ?
N2 C22 C221 . . 113.6(2) ?
N2 C22 H22A . . 108.8 ?
C221 C22 H22A . . 108.8 ?
N2 C22 H22B . . 108.8 ?
C221 C22 H22B . . 108.8 ?
H22A C22 H22B . . 107.7 ?
N2 C23 C231 . . 110.9(2) ?
N2 C23 H23A . . 109.5 ?
C231 C23 H23A . . 109.5 ?
N2 C23 H23B . . 109.5 ?
C231 C23 H23B . . 109.5 ?
H23A C23 H23B . . 108.0 ?
C242 C24 C241 . . 108.9(2) ?
C242 C24 C21 . . 110.4(2) ?
C241 C24 C21 . . 110.8(2) ?
C242 C24 H24 . . 108.9 ?
C241 C24 H24 . . 108.9 ?
C21 C24 H24 . . 108.9 ?
C216 C211 C212 . . 118.3(2) ?
C216 C211 C21 . . 119.2(2) ?
C212 C211 C21 . . 122.4(2) ?
C213 C212 C211 . . 120.8(2) ?
C213 C212 H212 . . 119.6 ?
C211 C212 H212 . . 119.6 ?
C214 C213 C212 . . 120.1(2) ?
C214 C213 H213 . . 119.9 ?
C212 C213 H213 . . 119.9 ?
C213 C214 C215 . . 120.2(2) ?
C213 C214 C217 . . 118.4(3) ?
C215 C214 C217 . . 121.3(3) ?
C214 C215 C216 . . 119.3(2) ?
C214 C215 H215 . . 120.4 ?
C216 C215 H215 . . 120.4 ?
C215 C216 C211 . . 121.4(2) ?
C215 C216 H216 . . 119.3 ?
C211 C216 H216 . . 119.3 ?
F21 C217 F22 . . 106.9(3) ?
F21 C217 F23 . . 106.9(3) ?
F22 C217 F23 . . 105.0(3) ?
F21 C217 C214 . . 114.0(3) ?
F22 C217 C214 . . 112.8(3) ?
F23 C217 C214 . . 110.6(3) ?
C222 C221 C226 . . 118.9(3) ?
C222 C221 C22 . . 121.0(3) ?
C226 C221 C22 . . 120.0(3) ?
C221 C222 C223 . . 120.1(3) ?
C221 C222 H222 . . 119.9 ?
C223 C222 H222 . . 119.9 ?
C224 C223 C222 . . 119.5(4) ?
C224 C223 H223 . . 120.2 ?
C222 C223 H223 . . 120.2 ?
C225 C224 C223 . . 120.6(3) ?
C225 C224 H224 . . 119.7 ?
C223 C224 H224 . . 119.7 ?
C224 C225 C226 . . 119.9(3) ?
C224 C225 H225 . . 120.0 ?
C226 C225 H225 . . 120.0 ?
C225 C226 C221 . . 121.0(3) ?
C225 C226 H226 . . 119.5 ?
C221 C226 H226 . . 119.5 ?
C232 C231 C236 . . 118.8(3) ?
C232 C231 C23 . . 120.1(3) ?
C236 C231 C23 . . 121.0(3) ?
C231 C232 C233 . . 119.5(4) ?
C231 C232 H232 . . 120.2 ?
C233 C232 H232 . . 120.2 ?
C232 C233 C234 . . 120.3(4) ?
C232 C233 H233 . . 119.8 ?
C234 C233 H233 . . 119.8 ?
C235 C234 C233 . . 119.9(3) ?
C235 C234 H234 . . 120.0 ?
C233 C234 H234 . . 120.0 ?
C234 C235 C236 . . 120.2(4) ?
C234 C235 H235 . . 119.9 ?
C236 C235 H235 . . 119.9 ?
C235 C236 C231 . . 121.2(4) ?
C235 C236 H236 . . 119.4 ?
C231 C236 H236 . . 119.4 ?
O24 C242 O23 . . 125.7(3) ?
O24 C242 C24 . . 123.9(3) ?
O23 C242 C24 . . 110.4(2) ?
O22 C241 O21 . . 123.1(3) ?
O22 C241 C24 . . 126.1(2) ?
O21 C241 C24 . . 110.8(2) ?
C241 O21 C243 . . 110.9(3) ?
C241 O21 C24A . . 127.0(6) ?
C243 O21 C24A . . 26.5(5) ?
C244 C243 O21 . . 106.2(5) ?
C244 C243 H24A . . 110.5 ?
O21 C243 H24A . . 110.5 ?
C244 C243 H24B . . 110.5 ?
O21 C243 H24B . . 110.5 ?
H24A C243 H24B . . 108.7 ?
C24B C24A O21 . . 82.1(12) ?
C24B C24A H24F . . 114.9 ?
O21 C24A H24F . . 114.9 ?
C24B C24A H24G . . 114.9 ?
O21 C24A H24G . . 114.9 ?
H24F C24A H24G . . 112.0 ?
C246 C245 O23 . . 109.9(3) ?
C246 C245 H24K . . 109.7 ?
O23 C245 H24K . . 109.7 ?
C246 C245 H24L . . 109.7 ?
O23 C245 H24L . . 109.7 ?
H24K C245 H24L . . 108.2 ?
C245 C246 H24M . . 109.5 ?
C245 C246 H24N . . 109.5 ?
H24M C246 H24N . . 109.5 ?
C245 C246 H24O . . 109.5 ?
H24M C246 H24O . . 109.5 ?
H24N C246 H24O . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C13 . 1.465(3) ?
N1 C12 . 1.469(3) ?
N1 C11 . 1.479(3) ?
O12 C141 . 1.187(4) ?
O13 C142 . 1.329(3) ?
O13 C145 . 1.454(3) ?
O14 C142 . 1.197(3) ?
F11 C117 . 1.265(4) ?
F12 C117 . 1.361(6) ?
F13 C117 . 1.295(5) ?
C11 C111 . 1.519(3) ?
C11 C14 . 1.538(3) ?
C11 H11 . 0.9800 ?
C12 C121 . 1.508(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C131 . 1.508(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C141 . 1.515(4) ?
C14 C142 . 1.519(4) ?
C14 H14 . 0.9800 ?
C111 C116 . 1.391(3) ?
C111 C112 . 1.392(3) ?
C112 C113 . 1.377(4) ?
C112 H112 . 0.9300 ?
C113 C114 . 1.382(4) ?
C113 H113 . 0.9300 ?
C114 C115 . 1.382(4) ?
C114 C117 . 1.487(5) ?
C115 C116 . 1.380(4) ?
C115 H115 . 0.9300 ?
C116 H116 . 0.9300 ?
C121 C122 . 1.383(4) ?
C121 C126 . 1.395(4) ?
C122 C123 . 1.394(4) ?
C122 H122 . 0.9300 ?
C123 C124 . 1.371(4) ?
C123 H123 . 0.9300 ?
C124 C125 . 1.373(5) ?
C124 H124 . 0.9300 ?
C125 C126 . 1.372(4) ?
C125 H125 . 0.9300 ?
C126 H126 . 0.9300 ?
C131 C136 . 1.382(4) ?
C131 C132 . 1.389(3) ?
C132 C133 . 1.379(4) ?
C132 H132 . 0.9300 ?
C133 C134 . 1.371(4) ?
C133 H133 . 0.9300 ?
C134 C135 . 1.380(4) ?
C134 H134 . 0.9300 ?
C135 C136 . 1.382(4) ?
C135 H135 . 0.9300 ?
C136 H136 . 0.9300 ?
C141 O11 . 1.330(4) ?
O11 C14A . 1.492(12) ?
O11 C143 . 1.504(10) ?
C143 C144 . 1.440(13) ?
C143 H14A . 0.9700 ?
C143 H14B . 0.9700 ?
C144 H14C . 0.9600 ?
C144 H14D . 0.9600 ?
C144 H14E . 0.9600 ?
C14B C14A . 1.430(13) ?
C14B H14F . 0.9600 ?
C14B H14G . 0.9600 ?
C14B H14H . 0.9600 ?
C14A H14I . 0.9700 ?
C14A H14J . 0.9700 ?
C145 C146 . 1.501(5) ?
C145 H14K . 0.9700 ?
C145 H14L . 0.9700 ?
C146 H14M . 0.9600 ?
C146 H14N . 0.9600 ?
C146 H14O . 0.9600 ?
N2 C23 . 1.470(3) ?
N2 C22 . 1.472(3) ?
N2 C21 . 1.479(3) ?
O22 C241 . 1.183(3) ?
O23 C242 . 1.337(3) ?
O23 C245 . 1.468(4) ?
O24 C242 . 1.197(3) ?
F21 C217 . 1.302(4) ?
F22 C217 . 1.331(4) ?
F23 C217 . 1.332(4) ?
C21 C211 . 1.518(3) ?
C21 C24 . 1.534(3) ?
C21 H21 . 0.9800 ?
C22 C221 . 1.501(4) ?
C22 H22A . 0.9700 ?
C22 H22B . 0.9700 ?
C23 C231 . 1.502(3) ?
C23 H23A . 0.9700 ?
C23 H23B . 0.9700 ?
C24 C242 . 1.518(4) ?
C24 C241 . 1.520(4) ?
C24 H24 . 0.9800 ?
C211 C216 . 1.384(3) ?
C211 C212 . 1.391(3) ?
C212 C213 . 1.379(4) ?
C212 H212 . 0.9300 ?
C213 C214 . 1.376(4) ?
C213 H213 . 0.9300 ?
C214 C215 . 1.383(4) ?
C214 C217 . 1.497(4) ?
C215 C216 . 1.384(4) ?
C215 H215 . 0.9300 ?
C216 H216 . 0.9300 ?
C221 C222 . 1.366(4) ?
C221 C226 . 1.385(4) ?
C222 C223 . 1.402(5) ?
C222 H222 . 0.9300 ?
C223 C224 . 1.371(5) ?
C223 H223 . 0.9300 ?
C224 C225 . 1.355(5) ?
C224 H224 . 0.9300 ?
C225 C226 . 1.374(4) ?
C225 H225 . 0.9300 ?
C226 H226 . 0.9300 ?
C231 C232 . 1.379(5) ?
C231 C236 . 1.383(4) ?
C232 C233 . 1.383(5) ?
C232 H232 . 0.9300 ?
C233 C234 . 1.384(7) ?
C233 H233 . 0.9300 ?
C234 C235 . 1.349(7) ?
C234 H234 . 0.9300 ?
C235 C236 . 1.366(5) ?
C235 H235 . 0.9300 ?
C236 H236 . 0.9300 ?
C241 O21 . 1.321(3) ?
O21 C243 . 1.522(6) ?
O21 C24A . 1.602(14) ?
C243 C244 . 1.430(8) ?
C243 H24A . 0.9700 ?
C243 H24B . 0.9700 ?
C244 H24C . 0.9600 ?
C244 H24D . 0.9600 ?
C244 H24E . 0.9600 ?
C24A C24B . 1.447(12) ?
C24A H24F . 0.9700 ?
C24A H24G . 0.9700 ?
C24B H24H . 0.9600 ?
C24B H24I . 0.9600 ?
C24B H24J . 0.9600 ?
C245 C246 . 1.449(5) ?
C245 H24K . 0.9700 ?
C245 H24L . 0.9700 ?
C246 H24M . 0.9600 ?
C246 H24N . 0.9600 ?
C246 H24O . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C226 H226 O22 3_665 0.93 2.60 3.323(4) 135 yes
C235 H235 O14 3_566 0.93 2.51 3.294(4) 142 yes
