#------------------------------------------------------------------------------
#$Date: 2020-07-08 08:10:32 +0300 (Wed, 08 Jul 2020) $
#$Revision: 254110 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243474.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_2243474
loop_
_publ_author_name
'Churchill, Serena B. S.'
'Sharma, Meenakshi'
'Brückner, Christian'
'Zeller, Matthias'
_publ_section_title
;
 Crystal structure of
 2,3-dimethoxy-meso-tetrakis(pentafluorophenyl)morpholinochlorin
 methylene chloride 0.44-solvate
;
_journal_coeditor_code           IS5543
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1222
_journal_page_last               1228
_journal_paper_doi               10.1107/S2056989020009093
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C46 H16 F20 N4 O3, 0.44C H2 Cl2'
_chemical_formula_moiety         'C46 H16 F20 N4 O3, 0.44(C H2 Cl2)'
_chemical_formula_sum            'C46.44 H16.88 Cl0.88 F20 N4 O3'
_chemical_formula_weight         1090.00
_chemical_name_systematic
;
2,3-Dimethoxy-meso-tetrakis(pentafluorophenyl)morpholinochlorin
methylene chloride 0.44-solvate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 113.1683(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.1774(10)
_cell_length_b                   15.4767(7)
_cell_length_c                   26.0442(13)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.2899
_cell_measurement_theta_min      3.0185
_cell_volume                     8588.9(7)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015) and
shelXle  (Hübschle et al., 2011)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 Quest CMOS '
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            52998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.312
_diffrn_reflns_theta_min         3.002
_diffrn_source                   'sealed tube X-ray source'
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_description       block
_exptl_crystal_F_000             4340
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.837
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     724
_refine_ls_number_reflns         10495
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0789P)²+8.8470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1644
_reflns_number_gt                6698
_reflns_number_total             10495
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            is5543sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2243474
_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   0.976
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.32635(11) 0.72878(15) 0.38040(10) 0.0219(5) Uani d 1 . .
C C2 0.32104(12) 0.68340(16) 0.43114(10) 0.0255(5) Uani d 1 . .
H H2 0.296174 0.629244 0.417471 0.031 Uiso calc 1 . .
C C3 0.24577(11) 0.79201(15) 0.42231(10) 0.0233(5) Uani d 1 . .
H H3 0.229375 0.828639 0.445218 0.028 Uiso calc 1 . .
C C4 0.27686(11) 0.85048(15) 0.39362(10) 0.0227(5) Uani d 1 . .
C C5 0.26559(12) 0.93899(15) 0.39395(11) 0.0247(5) Uani d 1 . .
C C6 0.29046(12) 1.00692(16) 0.37303(11) 0.0272(5) Uani d 1 . .
C C7 0.28844(13) 1.09651(16) 0.38542(12) 0.0321(6) Uani d 1 . .
H H7 0.268250 1.120434 0.407602 0.039 Uiso calc 1 . .
C C8 0.32024(13) 1.14180(16) 0.36019(12) 0.0313(6) Uani d 1 . .
H H8 0.327240 1.202425 0.362572 0.038 Uiso calc 1 . .
C C9 0.34121(12) 1.08218(15) 0.32952(11) 0.0268(5) Uani d 1 . .
C C10 0.37142(11) 1.10000(15) 0.29387(11) 0.0256(5) Uani d 1 . .
C C11 0.38331(11) 1.03995(15) 0.25895(10) 0.0236(5) Uani d 1 . .
C C12 0.40467(13) 1.06396(17) 0.21565(12) 0.0324(6) Uani d 1 . .
H H12 0.417330 1.119836 0.209104 0.039 Uiso calc 1 . .
C C13 0.40309(13) 0.99144(17) 0.18644(11) 0.0321(6) Uani d 1 . .
H H13 0.413110 0.986312 0.154535 0.039 Uiso calc 1 . .
C C14 0.38299(11) 0.92292(15) 0.21356(10) 0.0231(5) Uani d 1 . .
C C15 0.37907(11) 0.83510(15) 0.19838(10) 0.0215(5) Uani d 1 . .
C C16 0.36755(11) 0.76756(15) 0.22787(10) 0.0226(5) Uani d 1 . .
C C17 0.37311(13) 0.67770(16) 0.21961(11) 0.0318(6) Uani d 1 . .
H H17 0.380112 0.652305 0.189355 0.038 Uiso calc 1 . .
C C18 0.36671(13) 0.63440(16) 0.26236(12) 0.0323(6) Uani d 1 . .
H H18 0.369061 0.573502 0.267333 0.039 Uiso calc 1 . .
C C19 0.35586(11) 0.69561(15) 0.29864(10) 0.0231(5) Uani d 1 . .
C C20 0.34768(11) 0.67585(14) 0.34804(10) 0.0214(5) Uani d 1 . .
C C21 0.22315(12) 0.97069(15) 0.42126(11) 0.0271(5) Uani d 1 . .
C C22 0.24512(13) 0.99038(17) 0.47767(12) 0.0320(6) Uani d 1 . .
C C23 0.20658(14) 1.02359(18) 0.50208(12) 0.0360(6) Uani d 1 . .
C C24 0.14432(15) 1.0389(2) 0.46966(13) 0.0405(7) Uani d 1 . .
C C25 0.12069(14) 1.0214(2) 0.41347(13) 0.0417(7) Uani d 1 . .
C C26 0.16036(13) 0.98641(18) 0.39028(12) 0.0333(6) Uani d 1 . .
C C27 0.38931(12) 1.19202(15) 0.29033(11) 0.0256(5) Uani d 1 . .
C C28 0.34468(12) 1.25553(16) 0.26532(10) 0.0263(5) Uani d 1 . .
C C29 0.36086(13) 1.34043(16) 0.26142(11) 0.0287(5) Uani d 1 . .
C C30 0.42335(13) 1.36344(15) 0.28171(11) 0.0300(6) Uani d 1 . .
C C31 0.46876(13) 1.30227(18) 0.30576(13) 0.0338(6) Uani d 1 . .
C C32 0.45121(12) 1.21796(16) 0.30977(12) 0.0299(6) Uani d 1 . .
C C33 0.39339(11) 0.81235(15) 0.14862(10) 0.0229(5) Uani d 1 . .
C C34 0.45380(11) 0.81801(17) 0.15011(10) 0.0282(5) Uani d 1 . .
C C35 0.46780(12) 0.79981(18) 0.10433(11) 0.0313(6) Uani d 1 . .
C C36 0.42068(13) 0.77496(19) 0.05528(11) 0.0337(6) Uani d 1 . .
C C37 0.36041(13) 0.7670(2) 0.05249(11) 0.0365(6) Uani d 1 . .
C C38 0.34730(12) 0.78505(17) 0.09886(11) 0.0301(6) Uani d 1 . .
C C39 0.36233(11) 0.58285(15) 0.36504(10) 0.0219(5) Uani d 1 . .
C C40 0.31708(12) 0.51876(16) 0.34665(11) 0.0270(5) Uani d 1 . .
C C41 0.33125(13) 0.43302(16) 0.36056(11) 0.0291(6) Uani d 1 . .
C C42 0.39189(14) 0.41008(15) 0.39319(11) 0.0311(6) Uani d 1 . .
C C43 0.43823(13) 0.47182(17) 0.41231(11) 0.0302(6) Uani d 1 . .
C C44 0.42281(11) 0.55716(15) 0.39797(11) 0.0254(5) Uani d 1 . .
C C45 0.42137(13) 0.7312(2) 0.49423(12) 0.0377(6) Uani d 1 . .
H H45A 0.431108 0.757883 0.464446 0.057 Uiso calc 1 . .
H H45B 0.460179 0.710236 0.523699 0.057 Uiso calc 1 . .
H H45C 0.401672 0.774104 0.509843 0.057 Uiso calc 1 . .
C C46 0.15720(16) 0.7051(3) 0.40359(14) 0.0538(9) Uani d 1 . .
H H46A 0.119227 0.684073 0.373152 0.081 Uiso calc 1 . .
H H46B 0.145443 0.743803 0.427672 0.081 Uiso calc 1 . .
H H46C 0.180923 0.656005 0.425570 0.081 Uiso calc 1 . .
N N1 0.31243(9) 0.81349(13) 0.36912(9) 0.0229(4) Uani d 1 . .
N N2 0.32301(10) 1.00102(14) 0.33927(9) 0.0263(5) Uani d 1 . .
H H2A 0.3274(14) 0.954(2) 0.3242(13) 0.039(8) Uiso d 1 . .
N N3 0.37108(9) 0.95377(12) 0.25756(8) 0.0210(4) Uani d 1 . .
N N4 0.35551(9) 0.77493(13) 0.27530(9) 0.0211(4) Uani d 1 . .
H H4 0.3538(13) 0.8197(19) 0.2894(12) 0.028(8) Uiso d 1 . .
O O1 0.37925(9) 0.66032(12) 0.47187(8) 0.0325(4) Uani d 1 . .
O O2 0.29008(8) 0.73396(11) 0.45788(7) 0.0258(4) Uani d 1 . .
O O3 0.19528(8) 0.75125(12) 0.38073(8) 0.0309(4) Uani d 1 . .
F F1 0.30561(9) 0.97758(13) 0.50994(7) 0.0508(5) Uani d 1 . .
F F2 0.23007(9) 1.04108(13) 0.55689(7) 0.0536(5) Uani d 1 . .
F F3 0.10730(9) 1.07298(14) 0.49265(8) 0.0587(5) Uani d 1 . .
F F4 0.06062(9) 1.03781(17) 0.38111(9) 0.0701(7) Uani d 1 . .
F F5 0.13564(8) 0.97084(13) 0.33525(7) 0.0483(5) Uani d 1 . .
F F6 0.28370(7) 1.23508(10) 0.24473(7) 0.0360(4) Uani d 1 . .
F F7 0.31630(7) 1.40025(10) 0.23865(7) 0.0377(4) Uani d 1 . .
F F8 0.43987(8) 1.44566(10) 0.27921(8) 0.0423(4) Uani d 1 . .
F F9 0.52959(8) 1.32485(11) 0.32567(9) 0.0519(5) Uani d 1 . .
F F10 0.49729(7) 1.15998(10) 0.33406(8) 0.0446(4) Uani d 1 . .
F F11 0.50098(7) 0.84265(13) 0.19692(6) 0.0448(4) Uani d 1 . .
F F12 0.52687(7) 0.80701(13) 0.10779(7) 0.0463(4) Uani d 1 . .
F F13 0.43327(8) 0.75890(13) 0.01025(7) 0.0493(5) Uani d 1 . .
F F14 0.31452(8) 0.74177(15) 0.00464(7) 0.0586(6) Uani d 1 . .
F F15 0.28789(7) 0.77668(12) 0.09439(7) 0.0429(4) Uani d 1 . .
F F16 0.25774(7) 0.54003(10) 0.31493(7) 0.0408(4) Uani d 1 . .
F F17 0.28647(8) 0.37195(10) 0.34199(8) 0.0424(4) Uani d 1 . .
F F18 0.40620(9) 0.32672(9) 0.40659(7) 0.0430(4) Uani d 1 . .
F F19 0.49691(8) 0.44860(11) 0.44487(8) 0.0477(5) Uani d 1 . .
F F20 0.46884(7) 0.61620(9) 0.41722(7) 0.0355(4) Uani d 1 . .
C C47 0.4785(12) 0.980(4) 0.4881(10) 0.154(6) Uani d 0.241(5) A -1
H H47A 0.476482 0.922171 0.470843 0.184 Uiso calc 0.241(5) A -1
H H47B 0.454112 1.021606 0.458893 0.184 Uiso calc 0.241(5) A -1
Cl Cl1 0.5576(3) 1.0144(6) 0.5239(4) 0.160(4) Uani d 0.241(5) A -1
Cl Cl2 0.4511(5) 0.9757(6) 0.5439(5) 0.144(3) Uani d 0.241(5) A -1
C C48 0.508(3) 0.962(3) 0.4834(13) 0.142(7) Uani d 0.199(4) B -2
H H48A 0.553867 0.953404 0.498144 0.171 Uiso calc 0.199(4) B -2
H H48B 0.489108 0.905124 0.468872 0.171 Uiso calc 0.199(4) B -2
Cl Cl3 0.4912(6) 1.0246(8) 0.4255(4) 0.127(4) Uani d 0.199(4) B -2
Cl Cl4 0.4918(11) 0.9784(13) 0.5413(7) 0.204(6) Uani d 0.199(4) B -2
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'
Cl Cl 0.1484 0.1585 '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
N1 C1 C20 . . 123.2(2) ?
N1 C1 C2 . . 122.3(2) ?
C20 C1 C2 . . 114.6(2) ?
O1 C2 O2 . . 107.04(19) ?
O1 C2 C1 . . 112.86(19) ?
O2 C2 C1 . . 113.33(19) ?
O1 C2 H2 . . 107.8 ?
O2 C2 H2 . . 107.8 ?
C1 C2 H2 . . 107.8 ?
O3 C3 O2 . . 113.30(19) ?
O3 C3 C4 . . 107.60(19) ?
O2 C3 C4 . . 109.84(19) ?
O3 C3 H3 . . 108.7 ?
O2 C3 H3 . . 108.7 ?
C4 C3 H3 . . 108.7 ?
N1 C4 C5 . . 124.7(2) ?
N1 C4 C3 . . 118.3(2) ?
C5 C4 C3 . . 117.0(2) ?
C4 C5 C6 . . 128.7(2) ?
C4 C5 C21 . . 118.8(2) ?
C6 C5 C21 . . 112.5(2) ?
N2 C6 C5 . . 127.7(2) ?
N2 C6 C7 . . 106.6(2) ?
C5 C6 C7 . . 125.6(2) ?
C8 C7 C6 . . 108.6(2) ?
C8 C7 H7 . . 125.7 ?
C6 C7 H7 . . 125.7 ?
C7 C8 C9 . . 107.8(2) ?
C7 C8 H8 . . 126.1 ?
C9 C8 H8 . . 126.1 ?
N2 C9 C10 . . 125.0(2) ?
N2 C9 C8 . . 106.8(2) ?
C10 C9 C8 . . 128.1(2) ?
C9 C10 C11 . . 125.5(2) ?
C9 C10 C27 . . 117.0(2) ?
C11 C10 C27 . . 117.5(2) ?
N3 C11 C10 . . 125.1(2) ?
N3 C11 C12 . . 111.2(2) ?
C10 C11 C12 . . 123.4(2) ?
C13 C12 C11 . . 106.5(2) ?
C13 C12 H12 . . 126.7 ?
C11 C12 H12 . . 126.7 ?
C12 C13 C14 . . 106.1(2) ?
C12 C13 H13 . . 127.0 ?
C14 C13 H13 . . 127.0 ?
N3 C14 C15 . . 124.1(2) ?
N3 C14 C13 . . 111.3(2) ?
C15 C14 C13 . . 124.5(2) ?
C16 C15 C14 . . 125.3(2) ?
C16 C15 C33 . . 117.3(2) ?
C14 C15 C33 . . 117.2(2) ?
N4 C16 C15 . . 126.0(2) ?
N4 C16 C17 . . 106.3(2) ?
C15 C16 C17 . . 127.3(2) ?
C18 C17 C16 . . 108.3(2) ?
C18 C17 H17 . . 125.9 ?
C16 C17 H17 . . 125.9 ?
C17 C18 C19 . . 108.6(2) ?
C17 C18 H18 . . 125.7 ?
C19 C18 H18 . . 125.7 ?
N4 C19 C20 . . 128.5(2) ?
N4 C19 C18 . . 105.8(2) ?
C20 C19 C18 . . 125.7(2) ?
C1 C20 C19 . . 129.1(2) ?
C1 C20 C39 . . 118.4(2) ?
C19 C20 C39 . . 112.42(19) ?
C26 C21 C22 . . 116.4(2) ?
C26 C21 C5 . . 121.1(2) ?
C22 C21 C5 . . 122.5(2) ?
F1 C22 C23 . . 118.3(3) ?
F1 C22 C21 . . 119.4(2) ?
C23 C22 C21 . . 122.3(3) ?
F2 C23 C24 . . 120.5(2) ?
F2 C23 C22 . . 120.0(3) ?
C24 C23 C22 . . 119.5(3) ?
F3 C24 C25 . . 120.0(3) ?
F3 C24 C23 . . 119.8(3) ?
C25 C24 C23 . . 120.2(2) ?
F4 C25 C24 . . 120.9(2) ?
F4 C25 C26 . . 120.1(3) ?
C24 C25 C26 . . 119.0(3) ?
F5 C26 C21 . . 120.2(2) ?
F5 C26 C25 . . 117.2(3) ?
C21 C26 C25 . . 122.6(3) ?
C32 C27 C28 . . 116.2(2) ?
C32 C27 C10 . . 121.8(2) ?
C28 C27 C10 . . 121.9(2) ?
F6 C28 C29 . . 118.1(2) ?
F6 C28 C27 . . 119.7(2) ?
C29 C28 C27 . . 122.3(2) ?
F7 C29 C30 . . 120.1(2) ?
F7 C29 C28 . . 120.4(2) ?
C30 C29 C28 . . 119.5(2) ?
F8 C30 C31 . . 119.8(2) ?
F8 C30 C29 . . 120.3(2) ?
C31 C30 C29 . . 119.9(2) ?
F9 C31 C30 . . 119.8(2) ?
F9 C31 C32 . . 120.8(2) ?
C30 C31 C32 . . 119.4(2) ?
F10 C32 C27 . . 119.8(2) ?
F10 C32 C31 . . 117.5(2) ?
C27 C32 C31 . . 122.7(2) ?
C38 C33 C34 . . 116.4(2) ?
C38 C33 C15 . . 122.0(2) ?
C34 C33 C15 . . 121.6(2) ?
F11 C34 C35 . . 117.4(2) ?
F11 C34 C33 . . 119.9(2) ?
C35 C34 C33 . . 122.7(2) ?
F12 C35 C36 . . 120.3(2) ?
F12 C35 C34 . . 120.3(2) ?
C36 C35 C34 . . 119.4(2) ?
F13 C36 C35 . . 120.1(2) ?
F13 C36 C37 . . 120.3(2) ?
C35 C36 C37 . . 119.7(2) ?
F14 C37 C36 . . 119.6(2) ?
F14 C37 C38 . . 120.3(2) ?
C36 C37 C38 . . 120.2(2) ?
F15 C38 C33 . . 119.9(2) ?
F15 C38 C37 . . 118.3(2) ?
C33 C38 C37 . . 121.7(2) ?
C44 C39 C40 . . 117.0(2) ?
C44 C39 C20 . . 120.9(2) ?
C40 C39 C20 . . 122.1(2) ?
F16 C40 C41 . . 118.6(2) ?
F16 C40 C39 . . 119.5(2) ?
C41 C40 C39 . . 121.9(2) ?
F17 C41 C42 . . 119.9(2) ?
F17 C41 C40 . . 120.7(2) ?
C42 C41 C40 . . 119.4(2) ?
F18 C42 C41 . . 119.8(2) ?
F18 C42 C43 . . 119.7(2) ?
C41 C42 C43 . . 120.5(2) ?
F19 C43 C42 . . 119.8(2) ?
F19 C43 C44 . . 121.2(2) ?
C42 C43 C44 . . 119.0(2) ?
F20 C44 C43 . . 117.8(2) ?
F20 C44 C39 . . 119.9(2) ?
C43 C44 C39 . . 122.3(2) ?
O1 C45 H45A . . 109.5 ?
O1 C45 H45B . . 109.5 ?
H45A C45 H45B . . 109.5 ?
O1 C45 H45C . . 109.5 ?
H45A C45 H45C . . 109.5 ?
H45B C45 H45C . . 109.5 ?
O3 C46 H46A . . 109.5 ?
O3 C46 H46B . . 109.5 ?
H46A C46 H46B . . 109.5 ?
O3 C46 H46C . . 109.5 ?
H46A C46 H46C . . 109.5 ?
H46B C46 H46C . . 109.5 ?
C4 N1 C1 . . 116.4(2) ?
C6 N2 C9 . . 110.1(2) ?
C6 N2 H2A . . 123(2) ?
C9 N2 H2A . . 126(2) ?
C11 N3 C14 . . 104.84(19) ?
C19 N4 C16 . . 110.9(2) ?
C19 N4 H4 . . 125(2) ?
C16 N4 H4 . . 124(2) ?
C2 O1 C45 . . 114.4(2) ?
C3 O2 C2 . . 114.19(18) ?
C3 O3 C46 . . 111.6(2) ?
Cl1 C47 Cl2 . . 101.8(12) ?
Cl1 C47 H47A . . 111.4 ?
Cl2 C47 H47A . . 111.4 ?
Cl1 C47 H47B . . 111.4 ?
Cl2 C47 H47B . . 111.4 ?
H47A C47 H47B . . 109.3 ?
Cl3 C48 Cl4 . . 130(2) ?
Cl3 C48 H48A . . 104.7 ?
Cl4 C48 H48A . . 104.7 ?
Cl3 C48 H48B . . 104.7 ?
Cl4 C48 H48B . . 104.7 ?
H48A C48 H48B . . 105.7 ?
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
C1 N1 . 1.354(3) ?
C1 C20 . 1.398(3) ?
C1 C2 . 1.544(3) ?
C2 O1 . 1.395(3) ?
C2 O2 . 1.416(3) ?
C2 H2 . 1.0000 ?
C3 O3 . 1.394(3) ?
C3 O2 . 1.404(3) ?
C3 C4 . 1.523(3) ?
C3 H3 . 1.0000 ?
C4 N1 . 1.352(3) ?
C4 C5 . 1.395(3) ?
C5 C6 . 1.408(3) ?
C5 C21 . 1.505(3) ?
C6 N2 . 1.368(3) ?
C6 C7 . 1.429(3) ?
C7 C8 . 1.359(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.425(3) ?
C8 H8 . 0.9500 ?
C9 N2 . 1.380(3) ?
C9 C10 . 1.393(3) ?
C10 C11 . 1.401(3) ?
C10 C27 . 1.496(3) ?
C11 N3 . 1.361(3) ?
C11 C12 . 1.447(3) ?
C12 C13 . 1.348(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.449(3) ?
C13 H13 . 0.9500 ?
C14 N3 . 1.366(3) ?
C14 C15 . 1.409(3) ?
C15 C16 . 1.384(3) ?
C15 C33 . 1.501(3) ?
C16 N4 . 1.374(3) ?
C16 C17 . 1.421(3) ?
C17 C18 . 1.357(4) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.429(3) ?
C18 H18 . 0.9500 ?
C19 N4 . 1.368(3) ?
C19 C20 . 1.406(3) ?
C20 C39 . 1.505(3) ?
C21 C26 . 1.380(4) ?
C21 C22 . 1.386(4) ?
C22 F1 . 1.336(3) ?
C22 C23 . 1.383(4) ?
C23 F2 . 1.340(3) ?
C23 C24 . 1.376(4) ?
C24 F3 . 1.333(3) ?
C24 C25 . 1.373(4) ?
C25 F4 . 1.338(4) ?
C25 C26 . 1.393(4) ?
C26 F5 . 1.339(3) ?
C27 C32 . 1.380(4) ?
C27 C28 . 1.389(4) ?
C28 F6 . 1.338(3) ?
C28 C29 . 1.381(3) ?
C29 F7 . 1.339(3) ?
C29 C30 . 1.379(4) ?
C30 F8 . 1.338(3) ?
C30 C31 . 1.370(4) ?
C31 F9 . 1.343(3) ?
C31 C32 . 1.383(4) ?
C32 F10 . 1.347(3) ?
C33 C38 . 1.382(4) ?
C33 C34 . 1.388(3) ?
C34 F11 . 1.334(3) ?
C34 C35 . 1.382(4) ?
C35 F12 . 1.341(3) ?
C35 C36 . 1.369(4) ?
C36 F13 . 1.338(3) ?
C36 C37 . 1.376(4) ?
C37 F14 . 1.339(3) ?
C37 C38 . 1.385(4) ?
C38 F15 . 1.342(3) ?
C39 C44 . 1.383(3) ?
C39 C40 . 1.385(3) ?
C40 F16 . 1.337(3) ?
C40 C41 . 1.381(4) ?
C41 F17 . 1.345(3) ?
C41 C42 . 1.372(4) ?
C42 F18 . 1.344(3) ?
C42 C43 . 1.376(4) ?
C43 F19 . 1.338(3) ?
C43 C44 . 1.381(3) ?
C44 F20 . 1.343(3) ?
C45 O1 . 1.432(3) ?
C45 H45A . 0.9800 ?
C45 H45B . 0.9800 ?
C45 H45C . 0.9800 ?
C46 O3 . 1.434(3) ?
C46 H46A . 0.9800 ?
C46 H46B . 0.9800 ?
C46 H46C . 0.9800 ?
N2 H2A . 0.85(3) ?
N4 H4 . 0.79(3) ?
C47 Cl1 . 1.781(19) ?
C47 Cl2 . 1.80(2) ?
C47 H47A . 0.9900 ?
C47 H47B . 0.9900 ?
C48 Cl3 . 1.705(19) ?
C48 Cl4 . 1.708(18) ?
C48 H48A . 0.9900 ?
C48 H48B . 0.9900 ?
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
C8 H8 F18 1_565 0.95 2.59 3.424(3) 147 yes
C18 H18 F8 1_545 0.95 2.51 3.319(3) 143 yes
C45 H45A F12 2_655 0.98 2.55 3.519(3) 169 yes
C45 H45B F19 5_666 0.98 2.66 3.389(3) 132 yes
C45 H45A F20 . 0.98 2.82 3.184(3) 103 yes
C46 H46A F10 3_445 0.98 2.63 3.496(4) 148 yes
C46 H46C F1 7_566 0.98 2.60 3.505(4) 153 yes
C48 H48B F12 2_655 0.99 2.42 3.25(5) 141 yes
N2 H2A N1 . 0.85(3) 2.56(3) 3.040(3) 117(3) yes
N2 H2A N3 . 0.85(3) 2.33(3) 2.858(3) 121(3) yes
N4 H4 N1 . 0.79(3) 2.61(3) 3.040(3) 116(2) yes
N4 H4 N3 . 0.79(3) 2.33(3) 2.852(3) 125(3) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 O1 . . . . -111.2(2) ?
C20 C1 C2 O1 . . . . 67.6(3) ?
N1 C1 C2 O2 . . . . 10.7(3) ?
C20 C1 C2 O2 . . . . -170.5(2) ?
O3 C3 C4 N1 . . . . -74.8(3) ?
O2 C3 C4 N1 . . . . 49.0(3) ?
O3 C3 C4 C5 . . . . 104.3(2) ?
O2 C3 C4 C5 . . . . -131.9(2) ?
N1 C4 C5 C6 . . . . -4.2(4) ?
C3 C4 C5 C6 . . . . 176.8(3) ?
N1 C4 C5 C21 . . . . 177.9(2) ?
C3 C4 C5 C21 . . . . -1.1(3) ?
C4 C5 C6 N2 . . . . 12.1(5) ?
C21 C5 C6 N2 . . . . -169.9(3) ?
C4 C5 C6 C7 . . . . -165.1(3) ?
C21 C5 C6 C7 . . . . 12.9(4) ?
N2 C6 C7 C8 . . . . -1.1(3) ?
C5 C6 C7 C8 . . . . 176.6(3) ?
C6 C7 C8 C9 . . . . 2.1(3) ?
C7 C8 C9 N2 . . . . -2.3(3) ?
C7 C8 C9 C10 . . . . 174.6(3) ?
N2 C9 C10 C11 . . . . 5.7(4) ?
C8 C9 C10 C11 . . . . -170.7(3) ?
N2 C9 C10 C27 . . . . -178.0(2) ?
C8 C9 C10 C27 . . . . 5.6(4) ?
C9 C10 C11 N3 . . . . -4.9(4) ?
C27 C10 C11 N3 . . . . 178.7(2) ?
C9 C10 C11 C12 . . . . 168.7(3) ?
C27 C10 C11 C12 . . . . -7.6(4) ?
N3 C11 C12 C13 . . . . 2.2(3) ?
C10 C11 C12 C13 . . . . -172.2(2) ?
C11 C12 C13 C14 . . . . -2.1(3) ?
C12 C13 C14 N3 . . . . 1.5(3) ?
C12 C13 C14 C15 . . . . -175.6(2) ?
N3 C14 C15 C16 . . . . -5.2(4) ?
C13 C14 C15 C16 . . . . 171.5(2) ?
N3 C14 C15 C33 . . . . 179.7(2) ?
C13 C14 C15 C33 . . . . -3.5(4) ?
C14 C15 C16 N4 . . . . 2.9(4) ?
C33 C15 C16 N4 . . . . 177.9(2) ?
C14 C15 C16 C17 . . . . -169.0(3) ?
C33 C15 C16 C17 . . . . 6.1(4) ?
N4 C16 C17 C18 . . . . -2.1(3) ?
C15 C16 C17 C18 . . . . 171.0(3) ?
C16 C17 C18 C19 . . . . 0.9(3) ?
C17 C18 C19 N4 . . . . 0.6(3) ?
C17 C18 C19 C20 . . . . -179.1(2) ?
N1 C1 C20 C19 . . . . -3.4(4) ?
C2 C1 C20 C19 . . . . 177.8(2) ?
N1 C1 C20 C39 . . . . 179.3(2) ?
C2 C1 C20 C39 . . . . 0.5(3) ?
N4 C19 C20 C1 . . . . 12.6(4) ?
C18 C19 C20 C1 . . . . -167.7(3) ?
N4 C19 C20 C39 . . . . -170.0(2) ?
C18 C19 C20 C39 . . . . 9.7(3) ?
C4 C5 C21 C26 . . . . -95.9(3) ?
C6 C5 C21 C26 . . . . 85.8(3) ?
C4 C5 C21 C22 . . . . 87.8(3) ?
C6 C5 C21 C22 . . . . -90.4(3) ?
C26 C21 C22 F1 . . . . -179.3(2) ?
C5 C21 C22 F1 . . . . -2.9(4) ?
C26 C21 C22 C23 . . . . 0.3(4) ?
C5 C21 C22 C23 . . . . 176.7(2) ?
F1 C22 C23 F2 . . . . -0.8(4) ?
C21 C22 C23 F2 . . . . 179.6(2) ?
F1 C22 C23 C24 . . . . 178.8(3) ?
C21 C22 C23 C24 . . . . -0.8(4) ?
F2 C23 C24 F3 . . . . 1.4(4) ?
C22 C23 C24 F3 . . . . -178.3(3) ?
F2 C23 C24 C25 . . . . 179.5(3) ?
C22 C23 C24 C25 . . . . -0.1(4) ?
F3 C24 C25 F4 . . . . -0.2(5) ?
C23 C24 C25 F4 . . . . -178.4(3) ?
F3 C24 C25 C26 . . . . 179.5(3) ?
C23 C24 C25 C26 . . . . 1.3(5) ?
C22 C21 C26 F5 . . . . 178.6(2) ?
C5 C21 C26 F5 . . . . 2.2(4) ?
C22 C21 C26 C25 . . . . 1.0(4) ?
C5 C21 C26 C25 . . . . -175.5(3) ?
F4 C25 C26 F5 . . . . 0.2(4) ?
C24 C25 C26 F5 . . . . -179.5(3) ?
F4 C25 C26 C21 . . . . 177.9(3) ?
C24 C25 C26 C21 . . . . -1.8(5) ?
C9 C10 C27 C32 . . . . 113.0(3) ?
C11 C10 C27 C32 . . . . -70.3(3) ?
C9 C10 C27 C28 . . . . -69.5(3) ?
C11 C10 C27 C28 . . . . 107.1(3) ?
C32 C27 C28 F6 . . . . 179.1(2) ?
C10 C27 C28 F6 . . . . 1.5(4) ?
C32 C27 C28 C29 . . . . -1.8(4) ?
C10 C27 C28 C29 . . . . -179.4(2) ?
F6 C28 C29 F7 . . . . 1.4(4) ?
C27 C28 C29 F7 . . . . -177.8(2) ?
F6 C28 C29 C30 . . . . -179.3(2) ?
C27 C28 C29 C30 . . . . 1.5(4) ?
F7 C29 C30 F8 . . . . 0.5(4) ?
C28 C29 C30 F8 . . . . -178.8(2) ?
F7 C29 C30 C31 . . . . 179.0(2) ?
C28 C29 C30 C31 . . . . -0.3(4) ?
F8 C30 C31 F9 . . . . -1.3(4) ?
C29 C30 C31 F9 . . . . -179.8(2) ?
F8 C30 C31 C32 . . . . 178.0(2) ?
C29 C30 C31 C32 . . . . -0.5(4) ?
C28 C27 C32 F10 . . . . -179.4(2) ?
C10 C27 C32 F10 . . . . -1.8(4) ?
C28 C27 C32 C31 . . . . 0.9(4) ?
C10 C27 C32 C31 . . . . 178.5(3) ?
F9 C31 C32 F10 . . . . -0.3(4) ?
C30 C31 C32 F10 . . . . -179.5(2) ?
F9 C31 C32 C27 . . . . 179.4(3) ?
C30 C31 C32 C27 . . . . 0.2(4) ?
C16 C15 C33 C38 . . . . 74.6(3) ?
C14 C15 C33 C38 . . . . -109.9(3) ?
C16 C15 C33 C34 . . . . -105.7(3) ?
C14 C15 C33 C34 . . . . 69.8(3) ?
C38 C33 C34 F11 . . . . -179.0(2) ?
C15 C33 C34 F11 . . . . 1.2(4) ?
C38 C33 C34 C35 . . . . 1.7(4) ?
C15 C33 C34 C35 . . . . -178.1(2) ?
F11 C34 C35 F12 . . . . 0.1(4) ?
C33 C34 C35 F12 . . . . 179.4(2) ?
F11 C34 C35 C36 . . . . -179.5(3) ?
C33 C34 C35 C36 . . . . -0.1(4) ?
F12 C35 C36 F13 . . . . -1.0(4) ?
C34 C35 C36 F13 . . . . 178.6(3) ?
F12 C35 C36 C37 . . . . 179.3(3) ?
C34 C35 C36 C37 . . . . -1.1(4) ?
F13 C36 C37 F14 . . . . 1.0(4) ?
C35 C36 C37 F14 . . . . -179.3(3) ?
F13 C36 C37 C38 . . . . -178.9(3) ?
C35 C36 C37 C38 . . . . 0.8(5) ?
C34 C33 C38 F15 . . . . 179.0(2) ?
C15 C33 C38 F15 . . . . -1.3(4) ?
C34 C33 C38 C37 . . . . -2.0(4) ?
C15 C33 C38 C37 . . . . 177.8(3) ?
F14 C37 C38 F15 . . . . 0.0(4) ?
C36 C37 C38 F15 . . . . 179.8(3) ?
F14 C37 C38 C33 . . . . -179.1(3) ?
C36 C37 C38 C33 . . . . 0.8(4) ?
C1 C20 C39 C44 . . . . -94.8(3) ?
C19 C20 C39 C44 . . . . 87.5(3) ?
C1 C20 C39 C40 . . . . 88.2(3) ?
C19 C20 C39 C40 . . . . -89.5(3) ?
C44 C39 C40 F16 . . . . 179.6(2) ?
C20 C39 C40 F16 . . . . -3.2(4) ?
C44 C39 C40 C41 . . . . 0.3(4) ?
C20 C39 C40 C41 . . . . 177.4(2) ?
F16 C40 C41 F17 . . . . 0.9(4) ?
C39 C40 C41 F17 . . . . -179.8(2) ?
F16 C40 C41 C42 . . . . -179.8(2) ?
C39 C40 C41 C42 . . . . -0.5(4) ?
F17 C41 C42 F18 . . . . -0.2(4) ?
C40 C41 C42 F18 . . . . -179.5(2) ?
F17 C41 C42 C43 . . . . 179.7(2) ?
C40 C41 C42 C43 . . . . 0.4(4) ?
F18 C42 C43 F19 . . . . -1.2(4) ?
C41 C42 C43 F19 . . . . 178.9(2) ?
F18 C42 C43 C44 . . . . 179.7(2) ?
C41 C42 C43 C44 . . . . -0.2(4) ?
F19 C43 C44 F20 . . . . 0.8(4) ?
C42 C43 C44 F20 . . . . 179.9(2) ?
F19 C43 C44 C39 . . . . -179.1(2) ?
C42 C43 C44 C39 . . . . 0.0(4) ?
C40 C39 C44 F20 . . . . -179.9(2) ?
C20 C39 C44 F20 . . . . 2.9(3) ?
C40 C39 C44 C43 . . . . 0.0(4) ?
C20 C39 C44 C43 . . . . -177.2(2) ?
C5 C4 N1 C1 . . . . 169.9(2) ?
C3 C4 N1 C1 . . . . -11.1(3) ?
C20 C1 N1 C4 . . . . 162.6(2) ?
C2 C1 N1 C4 . . . . -18.7(3) ?
C5 C6 N2 C9 . . . . -178.0(3) ?
C7 C6 N2 C9 . . . . -0.4(3) ?
C10 C9 N2 C6 . . . . -175.4(3) ?
C8 C9 N2 C6 . . . . 1.6(3) ?
C10 C11 N3 C14 . . . . 173.1(2) ?
C12 C11 N3 C14 . . . . -1.2(3) ?
C15 C14 N3 C11 . . . . 177.0(2) ?
C13 C14 N3 C11 . . . . -0.1(3) ?
C20 C19 N4 C16 . . . . 177.7(2) ?
C18 C19 N4 C16 . . . . -2.1(3) ?
C15 C16 N4 C19 . . . . -170.6(2) ?
C17 C16 N4 C19 . . . . 2.6(3) ?
O2 C2 O1 C45 . . . . -66.4(2) ?
C1 C2 O1 C45 . . . . 59.0(3) ?
O3 C3 O2 C2 . . . . 64.5(2) ?
C4 C3 O2 C2 . . . . -55.9(3) ?
O1 C2 O2 C3 . . . . 153.83(19) ?
C1 C2 O2 C3 . . . . 28.8(3) ?
O2 C3 O3 C46 . . . . 67.4(3) ?
C4 C3 O3 C46 . . . . -171.0(2) ?

_cod_database_fobs_code 2243474
