#------------------------------------------------------------------------------
#$Date: 2019-11-26 08:22:15 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243052 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/32/4133215.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_4133215
loop_
_publ_author_name
'Hu, Bin'
'Bezpalko, Mark W.'
'Fei, Chao'
'Dickie, Diane A.'
'Foxman, Bruce M.'
'Deng, Li'
_publ_section_title
;
 Origin of and a Solution for Uneven Efficiency by Cinchona
 Alkaloid-Derived, Pseudoenantiomeric Catalysts for Asymmetric Reactions.
;
_journal_issue                   42
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13913
_journal_page_last               13920
_journal_paper_doi               10.1021/jacs.8b09010
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C56.91 H52.86 Br1 Cl1 N6.95 O2.55'
_chemical_formula_sum            'C56.91 H52.86 Br Cl N6.95 O2.55'
_chemical_formula_weight         990.26
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2015-08-25
_audit_creation_method           CRYSTALS_ver_14.61_build_00000
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   35.1304(10)
_cell_length_b                   11.2909(3)
_cell_length_c                   12.4040(4)
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    120
_cell_measurement_theta_max      26
_cell_measurement_theta_min      2
_cell_volume                     4920.1(2)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'USER DEFINED STRUCTURE SOLUTION'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.089
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            58861
_diffrn_reflns_theta_full        28.063
_diffrn_reflns_theta_max         28.063
_diffrn_reflns_theta_min         1.642
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.942
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2061.347
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.31
_refine_diff_density_min         -0.74
_refine_ls_abs_structure_details 'Flack (1983), 5315 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.136(15)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     629
_refine_ls_number_reflns         11942
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0852
_refine_ls_shift/su_max          0.0019763
_refine_ls_shift/su_mean         0.0001489
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² +21.81P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2160
_refine_ls_wR_factor_gt          0.2117
_refine_ls_wR_factor_ref         0.2160
_reflns_limit_h_max              46
_reflns_limit_h_min              -46
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                9895
_reflns_number_total             11942
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0985
_oxford_refine_ls_scale          0.11246(5)
_oxford_reflns_number_all        11942
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'binh_02_054_0ma in P2(1)2(1)2'
_cod_data_source_file            QD-1.cif
_cod_data_source_block           binh_02_054
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Other' was changed to
'other' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21 21 2 '
_cod_original_formula_sum        'C56.91 H52.86 Br1 Cl1 N6.95 O2.55'
_cod_database_code               4133215
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x+1/2,y+1/2,-z
-x,-y,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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.53468(4) 0.7537(2) 1.22732(12) 0.0374 0.505(4) Uani . . P 1 2
Br11 Br 0.53539(4) 0.8252(2) 1.25278(12) 0.0362 0.495(4) Uani . . P 1 1
Cl1 Cl 0.74902(4) 0.53925(11) 0.66625(10) 0.0259 1.0000 Uani . . . . .
O1 O 0.5755(2) 0.4010(8) 1.2754(7) 0.036(2) 0.547(8) Uiso . . P 2 1
O2 O 0.65783(9) 0.7271(3) 0.9290(3) 0.0182 1.0000 Uani . . . . .
O3 O 0.5460(4) 0.0264(11) 1.2978(10) 0.077(4) 0.547(8) Uiso . . P 2 1
O11 O 0.5643(2) 0.4448(8) 1.3053(7) 0.024(2) 0.453(8) Uiso . . P 2 2
N1 N 0.57427(10) 0.8086(3) 0.9325(3) 0.0169 1.0000 Uani . . . . .
N2 N 0.70087(12) 0.6890(4) 1.3140(4) 0.0223 1.0000 Uani . . . . .
N3 N 0.67508(10) 0.5323(4) 0.9540(3) 0.0155 1.0000 Uani . . . . .
N4 N 0.71803(11) 0.4399(4) 0.8332(4) 0.0182 1.0000 Uani . . . . .
N5 N 0.65763(18) 0.4009(6) 0.6404(5) 0.0495 1.0000 Uani . . . . .
N6 N 0.8471(2) 0.5444(11) 0.6385(9) 0.1141 1.0000 Uani . U . . .
N7 N 0.5000 1.0000 0.7281(7) 0.0434 1.0000 Uani S T . . .
N8 N 0.5876(4) 0.2011(14) 1.4811(13) 0.058(4) 0.453(8) Uiso . . P 2 2
C1 C 0.54173(13) 0.8875(4) 0.9685(5) 0.0213 1.0000 Uani . . . . .
C2 C 0.55684(15) 1.0080(4) 1.0066(5) 0.0265 1.0000 Uani . . . . .
C3 C 0.59745(14) 1.0232(4) 0.9657(5) 0.0294 1.0000 Uani . . . . .
C4 C 0.59707(15) 0.9973(5) 0.8433(5) 0.0284 1.0000 Uani . . . . .
C5 C 0.59001(13) 0.8627(4) 0.8293(4) 0.0193 1.0000 Uani . . . . .
C6 C 0.62288(13) 0.9346(4) 1.0235(5) 0.0207 1.0000 Uani . . . . .
C7 C 0.60397(13) 0.8128(4) 1.0234(4) 0.0169 1.0000 Uani . . . . .
C8 C 0.63311(13) 0.7118(4) 1.0223(4) 0.0175 1.0000 Uani . . . . .
C9 C 0.63276(18) 1.0309(5) 0.7845(6) 0.0421 1.0000 Uani . . . . .
C10 C 0.6321(3) 1.0979(7) 0.6982(8) 0.0700 1.0000 Uani . . . . .
C11 C 0.55988(13) 0.6811(4) 0.9149(4) 0.0202 1.0000 Uani . . . . .
C12 C 0.52790(13) 0.6692(4) 0.8365(4) 0.0199 1.0000 Uani . . . . .
C13 C 0.53676(16) 0.6540(4) 0.7238(4) 0.0248 1.0000 Uani . . . . .
C14 C 0.57495(18) 0.6351(6) 0.6843(5) 0.0345 1.0000 Uani . . . . .
C15 C 0.5823(2) 0.6251(6) 0.5785(6) 0.0486 1.0000 Uani . . . . .
C16 C 0.5531(3) 0.6345(7) 0.5038(6) 0.0590 1.0000 Uani . . . . .
C17 C 0.5173(3) 0.6478(8) 0.5353(6) 0.0570 1.0000 Uani . . . . .
C18 C 0.50691(18) 0.6525(6) 0.6477(5) 0.0349 1.0000 Uani . . . . .
C19 C 0.46991(18) 0.6560(6) 0.6803(5) 0.0386 1.0000 Uani . . . . .
C20 C 0.45988(15) 0.6575(5) 0.7904(5) 0.0271 1.0000 Uani . . . . .
C21 C 0.42116(17) 0.6478(5) 0.8238(6) 0.0393 1.0000 Uani . . . . .
C22 C 0.41209(16) 0.6488(5) 0.9286(6) 0.0396 1.0000 Uani . . . . .
C23 C 0.44098(16) 0.6570(5) 1.0086(6) 0.0341 1.0000 Uani . . . . .
C24 C 0.47810(15) 0.6652(5) 0.9783(5) 0.0252 1.0000 Uani . . . . .
C25 C 0.48961(14) 0.6653(4) 0.8691(4) 0.0215 1.0000 Uani . . . . .
C26 C 0.65565(13) 0.7082(4) 1.1250(4) 0.0184 1.0000 Uani . . . . .
C27 C 0.68847(14) 0.7712(5) 1.1381(5) 0.0245 1.0000 Uani . . . . .
C28 C 0.70915(14) 0.7603(5) 1.2334(4) 0.0235 1.0000 Uani . . . . .
C29 C 0.66891(14) 0.6207(4) 1.3015(4) 0.0192 1.0000 Uani . . . . .
C30 C 0.66079(17) 0.5385(5) 1.3828(5) 0.0288 1.0000 Uani . . . . .
C31 C 0.6288(2) 0.4691(6) 1.3779(5) 0.0396 1.0000 Uani . . . . .
C32 C 0.6029(2) 0.4846(8) 1.2910(5) 0.0549 1.0000 Uani . . . . .
C33 C 0.64415(13) 0.6302(4) 1.2106(4) 0.0186 1.0000 Uani . . . . .
C34 C 0.61080(16) 0.5612(6) 1.2093(5) 0.0313 1.0000 Uani . . . . .
C35 C 0.5695(4) 0.3098(12) 1.3498(11) 0.046(3) 0.547(8) Uiso . . P 2 1
C36 C 0.67843(13) 0.6311(4) 0.8979(4) 0.0150 1.0000 Uani . . . . .
C37 C 0.69593(12) 0.4400(4) 0.9206(4) 0.0132 1.0000 Uani . . . . .
C38 C 0.71980(13) 0.5410(4) 0.7790(4) 0.0170 1.0000 Uani . . . . .
C39 C 0.70149(13) 0.6449(4) 0.8077(4) 0.0147 1.0000 Uani . . . . .
C40 C 0.70777(12) 0.7594(4) 0.7509(4) 0.0162 1.0000 Uani . . . . .
C41 C 0.69650(14) 0.7770(5) 0.6450(5) 0.0272 1.0000 Uani . . . . .
C42 C 0.70669(18) 0.8816(6) 0.5919(5) 0.0380 1.0000 Uani . . . . .
C43 C 0.72820(17) 0.9661(6) 0.6432(6) 0.0410 1.0000 Uani . . . . .
C44 C 0.73870(15) 0.9485(5) 0.7482(5) 0.0324 1.0000 Uani . . . . .
C45 C 0.72840(13) 0.8470(4) 0.8030(4) 0.0205 1.0000 Uani . . . . .
C46 C 0.69420(12) 0.3306(4) 0.9870(4) 0.0154 1.0000 Uani . . . . .
C47 C 0.67790(14) 0.3331(5) 1.0887(4) 0.0227 1.0000 Uani . . . . .
C48 C 0.67745(14) 0.2308(5) 1.1517(4) 0.0240 1.0000 Uani . . . . .
C49 C 0.69312(15) 0.1280(5) 1.1128(4) 0.0237 1.0000 Uani . . . . .
C50 C 0.70895(15) 0.1251(5) 1.0114(5) 0.0258 1.0000 Uani . . . . .
C51 C 0.70939(14) 0.2255(5) 0.9475(4) 0.0238 1.0000 Uani . . . . .
C52 C 0.7029(3) 0.2769(7) 0.5245(8) 0.0725 1.0000 Uani . . . . .
C53 C 0.6771(2) 0.3442(7) 0.5879(6) 0.0461 1.0000 Uani . . . . .
C54 C 0.8646(2) 0.4745(13) 0.6093(9) 0.0995 1.0000 Uani . U . . .
C55 C 0.8866(3) 0.3783(8) 0.5687(12) 0.0882 1.0000 Uani . . . . .
C56 C 0.5000 1.0000 0.6441(10) 0.0442 1.0000 Uani S T . . .
C57 C 0.5000 1.0000 0.5264(11) 0.1130 1.0000 Uani S T . . .
C58 C 0.5776(4) 0.1819(13) 1.3974(11) 0.033(3) 0.453(8) Uiso . U P 2 2
C59 C 0.5657(4) 0.1507(14) 1.2864(12) 0.040(3) 0.453(8) Uiso . U P 2 2
C351 C 0.5309(3) 0.4874(11) 1.2453(11) 0.030(3) 0.453(8) Uiso . . P 2 2
H11 H 0.5291 0.8495 1.0289 0.0273 1.0000 Uiso R . . . .
H12 H 0.5240 0.8968 0.9078 0.0266 1.0000 Uiso R . . . .
H21 H 0.5565 1.0099 1.0847 0.0321 1.0000 Uiso R . . . .
H22 H 0.5408 1.0701 0.9792 0.0320 1.0000 Uiso R . . . .
H31 H 0.6063 1.1043 0.9795 0.0372 1.0000 Uiso R . . . .
H41 H 0.5759 1.0393 0.8112 0.0341 1.0000 Uiso R . . . .
H51 H 0.5723 0.8515 0.7704 0.0242 1.0000 Uiso R . . . .
H52 H 0.6138 0.8246 0.8128 0.0248 1.0000 Uiso R . . . .
H61 H 0.6474 0.9324 0.9884 0.0254 1.0000 Uiso R . . . .
H62 H 0.6257 0.9595 1.0989 0.0252 1.0000 Uiso R . . . .
H71 H 0.5898 0.8051 1.0901 0.0198 1.0000 Uiso R . . . .
H81 H 0.6186 0.6384 1.0129 0.0217 1.0000 Uiso R . . . .
H91 H 0.6563 1.0031 0.8101 0.0512 1.0000 Uiso R . . . .
H101 H 0.6543 1.1187 0.6639 0.0861 1.0000 Uiso R . . . .
H102 H 0.6093 1.1249 0.6707 0.0860 1.0000 Uiso R . . . .
H111 H 0.5528 0.6494 0.9852 0.0245 1.0000 Uiso R . . . .
H112 H 0.5815 0.6383 0.8870 0.0249 1.0000 Uiso R . . . .
H141 H 0.5952 0.6276 0.7349 0.0413 1.0000 Uiso R . . . .
H151 H 0.6071 0.6150 0.5552 0.0581 1.0000 Uiso R . . . .
H161 H 0.5586 0.6310 0.4307 0.0741 1.0000 Uiso R . . . .
H171 H 0.4983 0.6544 0.4835 0.0713 1.0000 Uiso R . . . .
H191 H 0.4502 0.6575 0.6287 0.0483 1.0000 Uiso R . . . .
H211 H 0.4018 0.6399 0.7728 0.0458 1.0000 Uiso R . . . .
H221 H 0.3869 0.6471 0.9493 0.0491 1.0000 Uiso R . . . .
H231 H 0.4342 0.6549 1.0805 0.0420 1.0000 Uiso R . . . .
H241 H 0.4964 0.6702 1.0312 0.0303 1.0000 Uiso R . . . .
H271 H 0.6972 0.8228 1.0837 0.0307 1.0000 Uiso R . . . .
H281 H 0.7311 0.8061 1.2390 0.0287 1.0000 Uiso R . . . .
H301 H 0.6768 0.5314 1.4419 0.0356 1.0000 Uiso R . . . .
H311 H 0.6248 0.4134 1.4306 0.0487 1.0000 Uiso R . . . .
H341 H 0.5944 0.5691 1.1513 0.0377 1.0000 Uiso R . . . .
H351 H 0.5625 0.3421 1.4180 0.0557 0.547(8) Uiso R . P 2 1
H352 H 0.5918 0.2636 1.3575 0.0557 0.547(8) Uiso R . P 2 1
H353 H 0.5492 0.2603 1.3249 0.0557 0.547(8) Uiso R . P 2 1
H411 H 0.6824 0.7186 0.6085 0.0331 1.0000 Uiso R . . . .
H421 H 0.6985 0.8942 0.5211 0.0468 1.0000 Uiso R . . . .
H431 H 0.7350 1.0362 0.6088 0.0502 1.0000 Uiso R . . . .
H441 H 0.7533 1.0058 0.7847 0.0406 1.0000 Uiso R . . . .
H451 H 0.7351 0.8387 0.8756 0.0255 1.0000 Uiso R . . . .
H471 H 0.6674 0.4025 1.1168 0.0277 1.0000 Uiso R . . . .
H481 H 0.6662 0.2305 1.2191 0.0301 1.0000 Uiso R . . . .
H491 H 0.6935 0.0606 1.1563 0.0288 1.0000 Uiso R . . . .
H501 H 0.7199 0.0538 0.9863 0.0309 1.0000 Uiso R . . . .
H511 H 0.7196 0.2247 0.8790 0.0290 1.0000 Uiso R . . . .
H521 H 0.6901 0.2070 0.4989 0.1109 1.0000 Uiso R . . . .
H522 H 0.7107 0.3246 0.4642 0.1112 1.0000 Uiso R . . . .
H523 H 0.7246 0.2562 0.5680 0.1109 1.0000 Uiso R . . . .
H551 H 0.9100 0.4057 0.5389 0.1037 1.0000 Uiso R . . . .
H552 H 0.8728 0.3374 0.5126 0.1037 1.0000 Uiso R . . . .
H553 H 0.8920 0.3228 0.6246 0.1037 1.0000 Uiso R . . . .
H571 H 0.5172 1.0595 0.5011 0.1397 0.5000 Uiso R . . . .
H572 H 0.4750 1.0187 0.5011 0.1397 0.5000 Uiso R . . . .
H573 H 0.5075 0.9255 0.5002 0.1397 0.5000 Uiso R . . . .
H591 H 0.5869 0.1221 1.2459 0.0494 0.453(8) Uiso R . P 2 2
H592 H 0.5555 0.2184 1.2513 0.0494 0.453(8) Uiso R . P 2 2
H593 H 0.5467 0.0901 1.2887 0.0494 0.453(8) Uiso R . P 2 2
H3511 H 0.5345 0.4721 1.1705 0.0353 0.453(8) Uiso R . P 2 2
H3512 H 0.5279 0.5703 1.2559 0.0353 0.453(8) Uiso R . P 2 2
H3513 H 0.5085 0.4478 1.2691 0.0353 0.453(8) Uiso R . P 2 2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C32 . O1 C35 . 121.6(9) yes
C8 . O2 C36 . 116.7(4) yes
C32 . O11 C351 . 125.9(8) yes
C1 . N1 C5 . 106.6(4) yes
C1 . N1 C7 . 106.1(4) yes
C5 . N1 C7 . 111.0(3) yes
C1 . N1 C11 . 110.1(3) yes
C5 . N1 C11 . 112.0(4) yes
C7 . N1 C11 . 110.8(3) yes
C28 . N2 C29 . 116.0(5) yes
C36 . N3 C37 . 116.5(4) yes
C37 . N4 C38 . 116.0(4) yes
N1 . C1 C2 . 110.5(4) yes
N1 . C1 H11 . 108.2 no
C2 . C1 H11 . 108.2 no
N1 . C1 H12 . 108.3 no
C2 . C1 H12 . 111.1 no
H11 . C1 H12 . 110.4 no
C1 . C2 C3 . 108.7(4) yes
C1 . C2 H21 . 108.9 no
C3 . C2 H21 . 110.0 no
C1 . C2 H22 . 109.5 no
C3 . C2 H22 . 110.4 no
H21 . C2 H22 . 109.3 no
C2 . C3 C4 . 107.3(5) yes
C2 . C3 C6 . 108.6(4) yes
C4 . C3 C6 . 110.1(4) yes
C2 . C3 H31 . 110.0 no
C4 . C3 H31 . 110.5 no
C6 . C3 H31 . 110.2 no
C3 . C4 C5 . 107.2(4) yes
C3 . C4 C9 . 115.0(5) yes
C5 . C4 C9 . 109.1(5) yes
C3 . C4 H41 . 108.5 no
C5 . C4 H41 . 108.1 no
C9 . C4 H41 . 108.7 no
C4 . C5 N1 . 111.0(4) yes
C4 . C5 H51 . 108.4 no
N1 . C5 H51 . 110.4 no
C4 . C5 H52 . 108.8 no
N1 . C5 H52 . 108.4 no
H51 . C5 H52 . 109.9 no
C3 . C6 C7 . 109.7(4) yes
C3 . C6 H61 . 109.2 no
C7 . C6 H61 . 111.4 no
C3 . C6 H62 . 108.7 no
C7 . C6 H62 . 107.7 no
H61 . C6 H62 . 110.2 no
N1 . C7 C6 . 108.9(4) yes
N1 . C7 C8 . 115.1(4) yes
C6 . C7 C8 . 112.3(4) yes
N1 . C7 H71 . 106.0 no
C6 . C7 H71 . 107.6 no
C8 . C7 H71 . 106.5 no
C7 . C8 O2 . 108.5(4) yes
C7 . C8 C26 . 111.4(4) yes
O2 . C8 C26 . 111.3(4) yes
C7 . C8 H81 . 106.4 no
O2 . C8 H81 . 108.4 no
C26 . C8 H81 . 110.6 no
C4 . C9 C10 . 121.9(7) yes
C4 . C9 H91 . 119.2 no
C10 . C9 H91 . 119.0 no
C9 . C10 H101 . 120.7 no
C9 . C10 H102 . 120.5 no
H101 . C10 H102 . 118.8 no
N1 . C11 C12 . 115.0(4) yes
N1 . C11 H111 . 107.4 no
C12 . C11 H111 . 110.9 no
N1 . C11 H112 . 105.1 no
C12 . C11 H112 . 108.3 no
H111 . C11 H112 . 109.8 no
C11 . C12 C13 . 118.7(4) yes
C11 . C12 C25 . 122.4(5) yes
C13 . C12 C25 . 118.8(5) yes
C12 . C13 C14 . 123.1(5) yes
C12 . C13 C18 . 119.3(5) yes
C14 . C13 C18 . 117.5(5) yes
C13 . C14 C15 . 121.5(7) yes
C13 . C14 H141 . 119.0 no
C15 . C14 H141 . 119.5 no
C14 . C15 C16 . 120.3(7) yes
C14 . C15 H151 . 119.9 no
C16 . C15 H151 . 119.8 no
C15 . C16 C17 . 120.9(7) yes
C15 . C16 H161 . 119.7 no
C17 . C16 H161 . 119.4 no
C16 . C17 C18 . 121.9(8) yes
C16 . C17 H171 . 119.2 no
C18 . C17 H171 . 118.9 no
C17 . C18 C13 . 117.3(6) yes
C17 . C18 C19 . 122.0(6) yes
C13 . C18 C19 . 120.7(6) yes
C18 . C19 C20 . 121.8(6) yes
C18 . C19 H191 . 120.0 no
C20 . C19 H191 . 118.2 no
C19 . C20 C21 . 121.3(6) yes
C19 . C20 C25 . 118.6(5) yes
C21 . C20 C25 . 120.1(5) yes
C20 . C21 C22 . 120.6(6) yes
C20 . C21 H211 . 120.4 no
C22 . C21 H211 . 119.0 no
C21 . C22 C23 . 120.5(5) yes
C21 . C22 H221 . 120.0 no
C23 . C22 H221 . 119.5 no
C22 . C23 C24 . 119.8(6) yes
C22 . C23 H231 . 119.3 no
C24 . C23 H231 . 121.0 no
C23 . C24 C25 . 122.6(6) yes
C23 . C24 H241 . 118.6 no
C25 . C24 H241 . 118.8 no
C20 . C25 C24 . 116.4(5) yes
C20 . C25 C12 . 120.3(5) yes
C24 . C25 C12 . 123.3(5) yes
C8 . C26 C27 . 122.2(5) yes
C8 . C26 C33 . 119.7(4) yes
C27 . C26 C33 . 118.0(5) yes
C26 . C27 C28 . 119.7(5) yes
C26 . C27 H271 . 120.8 no
C28 . C27 H271 . 119.4 no
C27 . C28 N2 . 125.7(5) yes
C27 . C28 H281 . 116.6 no
N2 . C28 H281 . 117.7 no
N2 . C29 C30 . 117.2(5) yes
N2 . C29 C33 . 123.1(5) yes
C30 . C29 C33 . 119.6(5) yes
C29 . C30 C31 . 120.9(5) yes
C29 . C30 H301 . 120.2 no
C31 . C30 H301 . 118.9 no
C30 . C31 C32 . 119.3(6) yes
C30 . C31 H311 . 119.0 no
C32 . C31 H311 . 121.8 no
C31 . C32 O1 . 118.4(7) yes
C31 . C32 C34 . 120.7(6) yes
O1 . C32 C34 . 118.6(6) yes
O11 . C32 C31 . 118.1(6) yes
O11 . C32 C34 . 118.9(7) yes
C31 . C32 C34 . 120.7(6) yes
C26 . C33 C29 . 117.3(4) yes
C26 . C33 C34 . 124.4(5) yes
C29 . C33 C34 . 118.3(5) yes
C33 . C34 C32 . 120.9(5) yes
C33 . C34 H341 . 118.3 no
C32 . C34 H341 . 120.8 no
O1 . C35 H351 . 110.0 no
O1 . C35 H352 . 110.3 no
H351 . C35 H352 . 109.4 no
O1 . C35 H353 . 109.2 no
H351 . C35 H353 . 108.7 no
H352 . C35 H353 . 109.2 no
O2 . C36 N3 . 118.5(4) yes
O2 . C36 C39 . 116.7(4) yes
N3 . C36 C39 . 124.8(4) yes
N3 . C37 N4 . 124.8(4) yes
N3 . C37 C46 . 117.0(4) yes
N4 . C37 C46 . 118.3(4) yes
Cl1 . C38 N4 . 115.3(4) yes
Cl1 . C38 C39 . 119.5(4) yes
N4 . C38 C39 . 125.2(4) yes
C36 . C39 C38 . 112.5(4) yes
C36 . C39 C40 . 124.3(4) yes
C38 . C39 C40 . 123.0(4) yes
C39 . C40 C41 . 122.0(5) yes
C39 . C40 C45 . 118.5(4) yes
C41 . C40 C45 . 119.3(5) yes
C40 . C41 C42 . 119.6(5) yes
C40 . C41 H411 . 120.4 no
C42 . C41 H411 . 120.0 no
C41 . C42 C43 . 120.6(6) yes
C41 . C42 H421 . 119.5 no
C43 . C42 H421 . 119.9 no
C42 . C43 C44 . 119.3(6) yes
C42 . C43 H431 . 121.3 no
C44 . C43 H431 . 119.4 no
C43 . C44 C45 . 121.2(6) yes
C43 . C44 H441 . 120.4 no
C45 . C44 H441 . 118.4 no
C40 . C45 C44 . 120.0(5) yes
C40 . C45 H451 . 120.6 no
C44 . C45 H451 . 119.4 no
C37 . C46 C47 . 120.3(4) yes
C37 . C46 C51 . 119.9(4) yes
C47 . C46 C51 . 119.8(5) yes
C46 . C47 C48 . 119.8(5) yes
C46 . C47 H471 . 121.4 no
C48 . C47 H471 . 118.8 no
C47 . C48 C49 . 120.0(5) yes
C47 . C48 H481 . 120.9 no
C49 . C48 H481 . 119.1 no
C48 . C49 C50 . 120.2(5) yes
C48 . C49 H491 . 119.5 no
C50 . C49 H491 . 120.2 no
C49 . C50 C51 . 120.6(5) yes
C49 . C50 H501 . 119.1 no
C51 . C50 H501 . 120.3 no
C46 . C51 C50 . 119.6(5) yes
C46 . C51 H511 . 118.8 no
C50 . C51 H511 . 121.6 no
C53 . C52 H521 . 108.8 no
C53 . C52 H522 . 108.2 no
H521 . C52 H522 . 109.7 no
C53 . C52 H523 . 108.9 no
H521 . C52 H523 . 110.8 no
H522 . C52 H523 . 110.5 no
C52 . C53 N5 . 177.1(8) yes
N6 . C54 C55 . 177.4(11) yes
C54 . C55 H551 . 111.0 no
C54 . C55 H552 . 110.3 no
H551 . C55 H552 . 108.0 no
C54 . C55 H553 . 110.6 no
H551 . C55 H553 . 109.0 no
H552 . C55 H553 . 108.0 no
N7 . C56 C57 . 179.992 yes
C56 . C57 H571 4_675 109.1 no
C56 . C57 H572 4_675 109.1 no
H571 4_675 C57 H572 4_675 108.5 no
C56 . C57 H573 4_675 110.2 no
H571 4_675 C57 H573 4_675 109.9 no
H572 4_675 C57 H573 4_675 109.9 no
C56 . C57 H571 . 109.1 no
H571 4_675 C57 H571 . 141.8 no
H572 4_675 C57 H571 . 57.8 no
H573 4_675 C57 H571 . 55.5 no
C56 . C57 H572 . 109.1 no
H571 4_675 C57 H572 . 57.8 no
H572 4_675 C57 H572 . 141.8 no
H573 4_675 C57 H572 . 55.5 no
H571 . C57 H572 . 108.5 no
C56 . C57 H573 . 110.2 no
H571 4_675 C57 H573 . 55.5 no
H572 4_675 C57 H573 . 55.5 no
H573 4_675 C57 H573 . 139.7 no
H571 . C57 H573 . 109.9 no
H572 . C57 H573 . 109.9 no
N8 . C58 C59 . 177.0(16) yes
C58 . C59 H591 . 110.4 no
C58 . C59 H592 . 110.0 no
H591 . C59 H592 . 109.0 no
C58 . C59 H593 . 109.9 no
H591 . C59 H593 . 108.6 no
H592 . C59 H593 . 108.9 no
O11 . C351 H3511 . 109.2 no
O11 . C351 H3512 . 110.0 no
H3511 . C351 H3512 . 109.1 no
O11 . C351 H3513 . 110.4 no
H3511 . C351 H3513 . 109.0 no
H3512 . C351 H3513 . 109.1 no
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
Cl1 C38 . 1.735(5) yes
O1 C32 . 1.361(10) yes
O1 C35 . 1.400(15) yes
O2 C8 . 1.457(5) yes
O2 C36 . 1.359(5) yes
O11 C32 . 1.438(11) yes
O11 C351 . 1.469(14) yes
N1 C1 . 1.517(6) yes
N1 C5 . 1.522(6) yes
N1 C7 . 1.537(6) yes
N1 C11 . 1.542(6) yes
N2 C28 . 1.317(7) yes
N2 C29 . 1.371(6) yes
N3 C36 . 1.320(6) yes
N3 C37 . 1.339(6) yes
N4 C37 . 1.334(6) yes
N4 C38 . 1.327(6) yes
N5 C53 . 1.140(10) yes
N6 C54 . 1.064(13) yes
N7 C56 . 1.043(13) yes
N8 C58 . 1.118(19) yes
C1 C2 . 1.535(7) yes
C1 H11 . 0.971 no
C1 H12 . 0.982 no
C2 C3 . 1.524(7) yes
C2 H21 . 0.968 no
C2 H22 . 0.962 no
C3 C4 . 1.547(9) yes
C3 C6 . 1.521(7) yes
C3 H31 . 0.982 no
C4 C5 . 1.550(7) yes
C4 C9 . 1.499(7) yes
C4 H41 . 0.969 no
C5 H51 . 0.969 no
C5 H52 . 0.963 no
C6 C7 . 1.528(6) yes
C6 H61 . 0.967 no
C6 H62 . 0.982 no
C7 C8 . 1.532(6) yes
C7 H71 . 0.968 no
C8 C26 . 1.500(7) yes
C8 H81 . 0.980 no
C9 C10 . 1.311(10) yes
C9 H91 . 0.938 no
C10 H101 . 0.919 no
C10 H102 . 0.924 no
C11 C12 . 1.491(7) yes
C11 H111 . 0.976 no
C11 H112 . 0.965 no
C12 C13 . 1.443(7) yes
C12 C25 . 1.405(7) yes
C13 C14 . 1.444(8) yes
C13 C18 . 1.411(8) yes
C14 C15 . 1.342(9) yes
C14 H141 . 0.954 no
C15 C16 . 1.387(12) yes
C15 H151 . 0.924 no
C16 C17 . 1.325(12) yes
C16 H161 . 0.928 no
C17 C18 . 1.442(10) yes
C17 H171 . 0.929 no
C18 C19 . 1.362(9) yes
C19 C20 . 1.411(9) yes
C19 H191 . 0.942 no
C20 C21 . 1.426(8) yes
C20 C25 . 1.432(7) yes
C21 C22 . 1.338(11) yes
C21 H211 . 0.933 no
C22 C23 . 1.422(10) yes
C22 H221 . 0.923 no
C23 C24 . 1.360(7) yes
C23 H231 . 0.923 no
C24 C25 . 1.414(7) yes
C24 H241 . 0.921 no
C26 C27 . 1.365(7) yes
C26 C33 . 1.437(7) yes
C27 C28 . 1.393(8) yes
C27 H271 . 0.943 no
C28 H281 . 0.931 no
C29 C30 . 1.400(8) yes
C29 C33 . 1.427(7) yes
C30 C31 . 1.372(8) yes
C30 H301 . 0.927 no
C31 C32 . 1.421(9) yes
C31 H311 . 0.918 no
C32 C34 . 1.361(8) yes
C32 C34 . 1.361(8) yes
C33 C34 . 1.407(7) yes
C34 H341 . 0.926 no
C35 H351 . 0.953 no
C35 H352 . 0.947 no
C35 H353 . 0.956 no
C36 C39 . 1.390(6) yes
C37 C46 . 1.486(6) yes
C38 C39 . 1.384(7) yes
C39 C40 . 1.489(6) yes
C40 C41 . 1.386(7) yes
C40 C45 . 1.386(7) yes
C41 C42 . 1.398(8) yes
C41 H411 . 0.940 no
C42 C43 . 1.374(10) yes
C42 H421 . 0.935 no
C43 C44 . 1.368(10) yes
C43 H431 . 0.932 no
C44 C45 . 1.381(7) yes
C44 H441 . 0.941 no
C45 H451 . 0.936 no
C46 C47 . 1.386(7) yes
C46 C51 . 1.390(7) yes
C47 C48 . 1.395(7) yes
C47 H471 . 0.933 no
C48 C49 . 1.371(8) yes
C48 H481 . 0.925 no
C49 C50 . 1.376(8) yes
C49 H491 . 0.932 no
C50 C51 . 1.383(7) yes
C50 H501 . 0.946 no
C51 H511 . 0.922 no
C52 C53 . 1.421(12) yes
C52 H521 . 0.962 no
C52 H522 . 0.960 no
C52 H523 . 0.963 no
C54 C55 . 1.425(14) yes
C55 H551 . 0.953 no
C55 H552 . 0.965 no
C55 H553 . 0.953 no
C56 C57 . 1.460(17) yes
C57 H571 4_675 0.956 no
C57 H572 4_675 0.956 no
C57 H573 4_675 0.939 no
C57 H571 . 0.956 no
C57 H572 . 0.956 no
C57 H573 . 0.939 no
C58 C59 . 1.48(2) yes
C59 H591 . 0.955 no
C59 H592 . 0.951 no
C59 H593 . 0.956 no
C351 H3511 . 0.953 no
C351 H3512 . 0.951 no
C351 H3513 . 0.953 no
