#------------------------------------------------------------------------------
#$Date: 2020-07-25 04:19:00 +0300 (Sat, 25 Jul 2020) $
#$Revision: 254568 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/86/1558664.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_1558664
loop_
_publ_author_name
'Heo, Nam Jung'
'Sessler, Jonathan L.'
'Ko, Byoung Joon'
'Kim, Sung Kuk'
'Yang, Ju Ho'
'Lynch, Vincent'
_publ_section_title
;
 Capture and displacement-based release of the bicarbonate anion by
 calix[4]pyrroles with small rigid straps
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03445B
_journal_year                    2020
_chemical_formula_moiety         'C45 H45 N5 O2'
_chemical_formula_sum            'C45 H45 N5 O2'
_chemical_formula_weight         687.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-21
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2020-06-18 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.6360(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9243(2)
_cell_length_b                   16.0575(2)
_cell_length_c                   18.3402(3)
_cell_measurement_reflns_used    13683
_cell_measurement_temperature    100.0(7)
_cell_measurement_theta_max      73.8460
_cell_measurement_theta_min      2.7190
_cell_volume                     3698.89(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'SHELXTL/XP, Bruker AXS, Inc. 2012'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2940
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  33.00   1.00    3.00    --  -41.59  38.00 150.00   99
  2  ω     39.00 136.00   1.00   10.00    --  108.34 -30.00 150.00   97
  3  ω    -74.00  24.00   1.00    3.00    --  -41.59  77.00   0.00   98
  4  ω     83.00 178.00   1.00   10.00    --  108.34  45.00-180.00   95
  5  ω    -70.00  31.00   1.00    3.00    --  -41.59  57.00-120.00  101
  6  ω     27.00  94.00   1.00   10.00    --  108.34 -94.00-150.00   67
  7  ω     43.00 136.00   1.00   10.00    --  108.34 -30.00   0.00   93
  8  ω     94.00 157.00   1.00   10.00    --  108.34 125.00  90.00   63
  9  ω     35.00 114.00   1.00   10.00    --  108.34-125.00 -30.00   79
 10  ω     66.00 117.00   1.00   10.00    --  108.34-125.00-150.00   51
 11  ω    102.00 178.00   1.00   10.00    --  108.34 125.00 120.00   76
 12  ω     32.00 134.00   1.00   10.00    --  108.34 -77.00  30.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1068538000
_diffrn_orient_matrix_UB_12      0.0418689000
_diffrn_orient_matrix_UB_13      0.0365397000
_diffrn_orient_matrix_UB_21      0.0355558000
_diffrn_orient_matrix_UB_22      -0.0795128000
_diffrn_orient_matrix_UB_23      0.0463904000
_diffrn_orient_matrix_UB_31      0.0482554000
_diffrn_orient_matrix_UB_32      -0.0336800000
_diffrn_orient_matrix_UB_33      -0.0632303000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21929
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.057
_diffrn_reflns_theta_min         3.705
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.332
_exptl_absorpt_correction_type   'gaussian and multi-scan'
_exptl_absorpt_process_details
;

CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       prism
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         7377
_refine_ls_number_restraints     312
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0488
_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)+(0.0785P)²+1.4379P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1328
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6860
_reflns_number_total             7377
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc03445b2.cif
_cod_data_source_block           njh-1vl
_cod_database_code               1558664
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_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.
;
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C39(H39A,H39B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N4(H4), C2(H2A), C3(H3A), C7(H7), C8(H8), C12(H12),
 C13(H13), C17(H17), C18(H18), C28(H28), C29(H29), C31(H31), C32(H32), C35(H35),
  C36(H36), C37(H37), C41(H41), C42(H42), C44(H44), C45(H45)
3.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.714
_oxdiff_exptl_absorpt_empirical_full_min 0.619
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
O1 O 0.71136(8) 0.72344(7) 0.61462(6) 0.0259(2) Uani 1 1 d . U . . .
O2 O 0.36347(8) 0.42008(6) 0.62828(6) 0.0253(2) Uani 1 1 d . U . . .
N1 N 0.13314(9) 0.83558(7) 0.60485(6) 0.0186(2) Uani 1 1 d . U . . .
H1 H 0.113384 0.841148 0.555792 0.022 Uiso 1 1 calc R U . . .
N2 N 0.29681(9) 0.92874(7) 0.52761(6) 0.0198(2) Uani 1 1 d . U . . .
H2 H 0.344166 0.899118 0.559518 0.024 Uiso 1 1 calc R U . . .
N3 N 0.19437(10) 0.79332(7) 0.37348(6) 0.0220(2) Uani 1 1 d . U . . .
H3 H 0.155685 0.824630 0.396190 0.026 Uiso 1 1 calc R U . . .
N4 N 0.07034(9) 0.68687(7) 0.46846(6) 0.0221(2) Uani 1 1 d . U . . .
H4 H 0.135510 0.666902 0.477164 0.026 Uiso 1 1 calc R U . . .
N5 N 0.58675(9) 0.54053(8) 0.66625(7) 0.0225(2) Uani 1 1 d . U . . .
C1 C 0.11434(10) 0.76639(8) 0.64375(8) 0.0189(3) Uani 1 1 d . U . . .
C2 C 0.15751(11) 0.78197(9) 0.71823(8) 0.0222(3) Uani 1 1 d . U . . .
H2A H 0.156500 0.745355 0.758741 0.027 Uiso 1 1 calc R U . . .
C3 C 0.20402(11) 0.86259(9) 0.72403(8) 0.0224(3) Uani 1 1 d . U . . .
H3A H 0.240331 0.889180 0.769086 0.027 Uiso 1 1 calc R U . . .
C4 C 0.18729(10) 0.89515(8) 0.65332(8) 0.0197(3) Uani 1 1 d . U . . .
C5 C 0.20842(11) 0.98158(8) 0.62683(8) 0.0216(3) Uani 1 1 d . U . . .
C6 C 0.21963(11) 0.97735(8) 0.54699(8) 0.0207(3) Uani 1 1 d . U . . .
C7 C 0.16280(11) 1.01295(9) 0.48197(9) 0.0247(3) Uani 1 1 d . U . . .
H7 H 0.104316 1.049965 0.477561 0.030 Uiso 1 1 calc R U . . .
C8 C 0.20672(11) 0.98476(9) 0.42221(8) 0.0251(3) Uani 1 1 d . U . . .
H8 H 0.182625 0.999428 0.370813 0.030 Uiso 1 1 calc R U . . .
C9 C 0.28993(11) 0.93271(8) 0.45191(8) 0.0202(3) Uani 1 1 d . U . . .
C10 C 0.36088(11) 0.88206(8) 0.41343(8) 0.0201(3) Uani 1 1 d . U . . .
C11 C 0.29723(11) 0.81043(8) 0.37025(7) 0.0200(3) Uani 1 1 d . U . . .
C12 C 0.32881(12) 0.74814(9) 0.32973(8) 0.0263(3) Uani 1 1 d . U . . .
H12 H 0.396295 0.743650 0.317889 0.032 Uiso 1 1 calc R U . . .
C13 C 0.24285(13) 0.69119(9) 0.30841(8) 0.0290(3) Uani 1 1 d . U . . .
H13 H 0.242678 0.641744 0.279936 0.035 Uiso 1 1 calc R U . . .
C14 C 0.16026(12) 0.72036(9) 0.33625(8) 0.0245(3) Uani 1 1 d . U . . .
C15 C 0.04770(13) 0.68911(10) 0.32813(8) 0.0294(3) Uani 1 1 d . U . . .
C16 C 0.00926(12) 0.70687(9) 0.39829(8) 0.0250(3) Uani 1 1 d . U . . .
C17 C -0.08514(12) 0.73664(9) 0.40897(9) 0.0296(3) Uani 1 1 d . U . . .
H17 H -0.143222 0.755895 0.370740 0.036 Uiso 1 1 calc R U . . .
C18 C -0.08167(12) 0.73392(9) 0.48723(9) 0.0274(3) Uani 1 1 d . U . . .
H18 H -0.136689 0.750854 0.510389 0.033 Uiso 1 1 calc R U . . .
C19 C 0.01582(11) 0.70231(8) 0.52296(8) 0.0201(3) Uani 1 1 d . U . . .
C20 C 0.06545(10) 0.68717(8) 0.60545(7) 0.0188(3) Uani 1 1 d . U . . .
C21 C 0.11440(12) 1.03857(9) 0.63070(9) 0.0276(3) Uani 1 1 d . U . . .
H21A H 0.048401 1.014798 0.600262 0.041 Uiso 1 1 calc R U . . .
H21B H 0.125947 1.093853 0.611406 0.041 Uiso 1 1 calc R U . . .
H21C H 0.108855 1.043422 0.682913 0.041 Uiso 1 1 calc R U . . .
C22 C 0.31035(12) 1.01762(9) 0.67837(9) 0.0276(3) Uani 1 1 d . U . . .
H22A H 0.303083 1.017743 0.730365 0.041 Uiso 1 1 calc R U . . .
H22B H 0.321180 1.074741 0.662873 0.041 Uiso 1 1 calc R U . . .
H22C H 0.371576 0.983287 0.674634 0.041 Uiso 1 1 calc R U . . .
C23 C 0.39883(12) 0.93928(9) 0.35731(8) 0.0272(3) Uani 1 1 d . U . . .
H23A H 0.336972 0.960362 0.320195 0.041 Uiso 1 1 calc R U . . .
H23B H 0.444697 0.907634 0.331749 0.041 Uiso 1 1 calc R U . . .
H23C H 0.438913 0.986188 0.384342 0.041 Uiso 1 1 calc R U . . .
C24 C -0.02694(14) 0.73199(14) 0.26092(10) 0.0446(5) Uani 1 1 d . U . . .
H24A H -0.023895 0.792436 0.268493 0.067 Uiso 1 1 calc R U . . .
H24B H -0.100012 0.712516 0.256527 0.067 Uiso 1 1 calc R U . . .
H24C H -0.004479 0.718351 0.214887 0.067 Uiso 1 1 calc R U . . .
C25 C 0.04548(17) 0.59440(11) 0.31416(9) 0.0407(4) Uani 1 1 d . U . . .
H25A H 0.068477 0.582822 0.267935 0.061 Uiso 1 1 calc R U . . .
H25B H -0.027092 0.573492 0.309187 0.061 Uiso 1 1 calc R U . . .
H25C H 0.093644 0.566661 0.356477 0.061 Uiso 1 1 calc R U . . .
C26 C -0.02182(11) 0.65837(9) 0.64494(9) 0.0268(3) Uani 1 1 d . U . . .
H26A H 0.010219 0.647919 0.698116 0.040 Uiso 1 1 calc R U . . .
H26B H -0.054785 0.607079 0.621334 0.040 Uiso 1 1 calc R U . . .
H26C H -0.076140 0.701886 0.640367 0.040 Uiso 1 1 calc R U . . .
C27 C 0.45456(10) 0.84325(8) 0.47116(7) 0.0192(3) Uani 1 1 d . U . . .
C28 C 0.55999(11) 0.86927(9) 0.48040(9) 0.0244(3) Uani 1 1 d . U . . .
H28 H 0.575165 0.915865 0.452742 0.029 Uiso 1 1 calc R U . . .
C29 C 0.64270(11) 0.82870(9) 0.52889(9) 0.0259(3) Uani 1 1 d . U . . .
H29 H 0.713743 0.847337 0.533643 0.031 Uiso 1 1 calc R U . . .
C30 C 0.62304(10) 0.76092(9) 0.57077(8) 0.0213(3) Uani 1 1 d . U . . .
C31 C 0.51828(10) 0.73554(8) 0.56520(7) 0.0194(3) Uani 1 1 d . U . . .
H31 H 0.503159 0.690988 0.595156 0.023 Uiso 1 1 calc R U . . .
C32 C 0.43607(10) 0.77636(8) 0.51516(7) 0.0184(3) Uani 1 1 d . U . . .
H32 H 0.364963 0.758071 0.510789 0.022 Uiso 1 1 calc R U . . .
C33 C 0.69533(11) 0.66199(10) 0.66723(8) 0.0252(3) Uani 1 1 d . U . . .
H33A H 0.644257 0.684092 0.695019 0.030 Uiso 1 1 calc R U . . .
H33B H 0.763749 0.652262 0.704002 0.030 Uiso 1 1 calc R U . . .
C34 C 0.65411(10) 0.57980(9) 0.63234(7) 0.0216(3) Uani 1 1 d . U . . .
C35 C 0.68436(11) 0.54704(9) 0.57035(8) 0.0241(3) Uani 1 1 d . U . . .
H35 H 0.732330 0.576288 0.547527 0.029 Uiso 1 1 calc R U . . .
C36 C 0.64302(12) 0.47093(9) 0.54273(8) 0.0258(3) Uani 1 1 d . U . . .
H36 H 0.662821 0.446765 0.500727 0.031 Uiso 1 1 calc R U . . .
C37 C 0.57263(12) 0.43021(9) 0.57667(8) 0.0244(3) Uani 1 1 d . U . . .
H37 H 0.542856 0.378047 0.558236 0.029 Uiso 1 1 calc R U . . .
C38 C 0.54636(11) 0.46731(9) 0.63840(8) 0.0223(3) Uani 1 1 d . U . . .
C39 C 0.46882(12) 0.42597(9) 0.67655(8) 0.0261(3) Uani 1 1 d . U . . .
H39A H 0.494796 0.369343 0.692676 0.031 Uiso 1 1 calc R U . . .
H39B H 0.465396 0.458120 0.721978 0.031 Uiso 1 1 calc R U . . .
C40 C 0.29861(11) 0.48802(8) 0.62410(7) 0.0197(3) Uani 1 1 d . U . . .
C41 C 0.33202(10) 0.56689(8) 0.65017(7) 0.0189(3) Uani 1 1 d . U . . .
H41 H 0.404991 0.577128 0.672566 0.023 Uiso 1 1 calc R U . . .
C42 C 0.25769(10) 0.63108(8) 0.64328(7) 0.0174(3) Uani 1 1 d . U . . .
H42 H 0.281288 0.685208 0.660452 0.021 Uiso 1 1 calc R U . . .
C43 C 0.15006(10) 0.61812(8) 0.61199(7) 0.0167(3) Uani 1 1 d . U . . .
C44 C 0.11878(10) 0.53823(8) 0.58490(7) 0.0190(3) Uani 1 1 d . U . . .
H44 H 0.045918 0.528033 0.562140 0.023 Uiso 1 1 calc R U . . .
C45 C 0.19110(11) 0.47391(8) 0.59042(7) 0.0209(3) Uani 1 1 d . U . . .
H45 H 0.167985 0.420295 0.571435 0.025 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C30 O1 C33 117.78(11) . . ?
C40 O2 C39 117.39(11) . . ?
C1 N1 H1 124.7 . . ?
C1 N1 C4 110.58(11) . . ?
C4 N1 H1 124.7 . . ?
C6 N2 H2 124.5 . . ?
C9 N2 H2 124.5 . . ?
C9 N2 C6 110.90(11) . . ?
C11 N3 H3 124.8 . . ?
C11 N3 C14 110.46(12) . . ?
C14 N3 H3 124.8 . . ?
C16 N4 H4 124.5 . . ?
C19 N4 H4 124.5 . . ?
C19 N4 C16 110.96(12) . . ?
C38 N5 C34 118.28(12) . . ?
N1 C1 C20 122.92(12) . . ?
C2 C1 N1 106.85(12) . . ?
C2 C1 C20 129.89(12) . . ?
C1 C2 H2A 126.1 . . ?
C1 C2 C3 107.85(12) . . ?
C3 C2 H2A 126.1 . . ?
C2 C3 H3A 126.0 . . ?
C4 C3 C2 107.93(12) . . ?
C4 C3 H3A 126.0 . . ?
N1 C4 C5 122.06(12) . . ?
C3 C4 N1 106.79(12) . . ?
C3 C4 C5 130.82(12) . . ?
C4 C5 C21 109.04(11) . . ?
C4 C5 C22 109.85(12) . . ?
C6 C5 C4 109.63(11) . . ?
C6 C5 C21 109.28(12) . . ?
C6 C5 C22 110.41(11) . . ?
C21 C5 C22 108.60(12) . . ?
N2 C6 C5 121.18(12) . . ?
C7 C6 N2 106.51(12) . . ?
C7 C6 C5 132.28(13) . . ?
C6 C7 H7 126.0 . . ?
C6 C7 C8 107.99(13) . . ?
C8 C7 H7 126.0 . . ?
C7 C8 H8 126.1 . . ?
C9 C8 C7 107.84(13) . . ?
C9 C8 H8 126.1 . . ?
N2 C9 C10 122.92(12) . . ?
C8 C9 N2 106.76(12) . . ?
C8 C9 C10 130.22(13) . . ?
C9 C10 C11 109.56(11) . . ?
C9 C10 C23 108.22(11) . . ?
C9 C10 C27 111.12(11) . . ?
C11 C10 C23 108.69(11) . . ?
C11 C10 C27 107.02(11) . . ?
C27 C10 C23 112.19(11) . . ?
N3 C11 C10 122.60(12) . . ?
C12 C11 N3 107.09(12) . . ?
C12 C11 C10 129.97(13) . . ?
C11 C12 H12 126.1 . . ?
C11 C12 C13 107.87(14) . . ?
C13 C12 H12 126.1 . . ?
C12 C13 H13 126.1 . . ?
C14 C13 C12 107.74(13) . . ?
C14 C13 H13 126.1 . . ?
N3 C14 C15 121.32(14) . . ?
C13 C14 N3 106.84(13) . . ?
C13 C14 C15 131.73(14) . . ?
C14 C15 C24 109.72(12) . . ?
C14 C15 C25 108.87(15) . . ?
C16 C15 C14 110.79(12) . . ?
C16 C15 C24 109.15(15) . . ?
C16 C15 C25 109.31(12) . . ?
C24 C15 C25 108.97(14) . . ?
N4 C16 C15 121.30(14) . . ?
C17 C16 N4 106.35(13) . . ?
C17 C16 C15 132.19(13) . . ?
C16 C17 H17 125.8 . . ?
C16 C17 C18 108.43(13) . . ?
C18 C17 H17 125.8 . . ?
C17 C18 H18 126.3 . . ?
C19 C18 C17 107.41(14) . . ?
C19 C18 H18 126.3 . . ?
N4 C19 C20 121.84(12) . . ?
C18 C19 N4 106.84(13) . . ?
C18 C19 C20 131.28(13) . . ?
C1 C20 C19 111.06(11) . . ?
C1 C20 C26 107.69(11) . . ?
C1 C20 C43 110.89(11) . . ?
C19 C20 C26 109.33(11) . . ?
C19 C20 C43 108.55(11) . . ?
C43 C20 C26 109.29(11) . . ?
C5 C21 H21A 109.5 . . ?
C5 C21 H21B 109.5 . . ?
C5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C5 C22 H22A 109.5 . . ?
C5 C22 H22B 109.5 . . ?
C5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C23 H23A 109.5 . . ?
C10 C23 H23B 109.5 . . ?
C10 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 C25 H25A 109.5 . . ?
C15 C25 H25B 109.5 . . ?
C15 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C20 C26 H26A 109.5 . . ?
C20 C26 H26B 109.5 . . ?
C20 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C10 123.28(12) . . ?
C28 C27 C32 117.04(13) . . ?
C32 C27 C10 119.63(11) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 C27 121.43(13) . . ?
C29 C28 H28 119.3 . . ?
C28 C29 H29 119.7 . . ?
C28 C29 C30 120.69(12) . . ?
C30 C29 H29 119.7 . . ?
O1 C30 C29 115.64(12) . . ?
O1 C30 C31 125.07(13) . . ?
C29 C30 C31 119.29(13) . . ?
C30 C31 H31 120.4 . . ?
C32 C31 C30 119.17(13) . . ?
C32 C31 H31 120.4 . . ?
C27 C32 H32 118.9 . . ?
C31 C32 C27 122.29(12) . . ?
C31 C32 H32 118.9 . . ?
O1 C33 H33A 108.7 . . ?
O1 C33 H33B 108.7 . . ?
O1 C33 C34 114.25(11) . . ?
H33A C33 H33B 107.6 . . ?
C34 C33 H33A 108.7 . . ?
C34 C33 H33B 108.7 . . ?
N5 C34 C33 114.70(12) . . ?
N5 C34 C35 122.69(14) . . ?
C35 C34 C33 122.61(13) . . ?
C34 C35 H35 120.8 . . ?
C36 C35 C34 118.41(14) . . ?
C36 C35 H35 120.8 . . ?
C35 C36 H36 120.3 . . ?
C35 C36 C37 119.49(13) . . ?
C37 C36 H36 120.3 . . ?
C36 C37 H37 120.8 . . ?
C36 C37 C38 118.49(14) . . ?
C38 C37 H37 120.8 . . ?
N5 C38 C37 122.63(13) . . ?
N5 C38 C39 116.93(12) . . ?
C37 C38 C39 120.44(13) . . ?
O2 C39 C38 112.30(11) . . ?
O2 C39 H39A 109.1 . . ?
O2 C39 H39B 109.1 . . ?
C38 C39 H39A 109.1 . . ?
C38 C39 H39B 109.1 . . ?
H39A C39 H39B 107.9 . . ?
O2 C40 C41 124.94(12) . . ?
O2 C40 C45 115.31(12) . . ?
C41 C40 C45 119.75(12) . . ?
C40 C41 H41 120.3 . . ?
C40 C41 C42 119.48(12) . . ?
C42 C41 H41 120.3 . . ?
C41 C42 H42 119.1 . . ?
C43 C42 C41 121.88(12) . . ?
C43 C42 H42 119.1 . . ?
C42 C43 C20 123.16(11) . . ?
C42 C43 C44 117.44(12) . . ?
C44 C43 C20 119.40(11) . . ?
C43 C44 H44 119.2 . . ?
C45 C44 C43 121.70(12) . . ?
C45 C44 H44 119.2 . . ?
C40 C45 H45 120.1 . . ?
C44 C45 C40 119.72(12) . . ?
C44 C45 H45 120.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C30 1.3708(17) . ?
O1 C33 1.4289(19) . ?
O2 C39 1.4415(18) . ?
O2 C40 1.3670(16) . ?
N1 H1 0.8800 . ?
N1 C1 1.3725(17) . ?
N1 C4 1.3790(17) . ?
N2 H2 0.8800 . ?
N2 C6 1.3775(18) . ?
N2 C9 1.3717(18) . ?
N3 H3 0.8800 . ?
N3 C11 1.3724(18) . ?
N3 C14 1.3753(18) . ?
N4 H4 0.8800 . ?
N4 C16 1.3796(17) . ?
N4 C19 1.3744(19) . ?
N5 C34 1.3407(19) . ?
N5 C38 1.338(2) . ?
C1 C2 1.3713(19) . ?
C1 C20 1.5170(18) . ?
C2 H2A 0.9500 . ?
C2 C3 1.421(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.367(2) . ?
C4 C5 1.5164(19) . ?
C5 C6 1.507(2) . ?
C5 C21 1.5362(19) . ?
C5 C22 1.5416(19) . ?
C6 C7 1.369(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.422(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.370(2) . ?
C9 C10 1.5185(19) . ?
C10 C11 1.5230(18) . ?
C10 C23 1.5435(18) . ?
C10 C27 1.5398(19) . ?
C11 C12 1.365(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.421(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.370(2) . ?
C14 C15 1.513(2) . ?
C15 C16 1.512(2) . ?
C15 C24 1.537(2) . ?
C15 C25 1.541(2) . ?
C16 C17 1.367(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.426(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.3729(19) . ?
C19 C20 1.5173(18) . ?
C20 C26 1.5477(18) . ?
C20 C43 1.5420(18) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.3968(19) . ?
C27 C32 1.3974(19) . ?
C28 H28 0.9500 . ?
C28 C29 1.382(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.390(2) . ?
C30 C31 1.3945(18) . ?
C31 H31 0.9500 . ?
C31 C32 1.3932(19) . ?
C32 H32 0.9500 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.508(2) . ?
C34 C35 1.390(2) . ?
C35 H35 0.9500 . ?
C35 C36 1.381(2) . ?
C36 H36 0.9500 . ?
C36 C37 1.382(2) . ?
C37 H37 0.9500 . ?
C37 C38 1.391(2) . ?
C38 C39 1.505(2) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.3863(19) . ?
C40 C45 1.400(2) . ?
C41 H41 0.9500 . ?
C41 C42 1.3942(19) . ?
C42 H42 0.9500 . ?
C42 C43 1.3896(18) . ?
C43 C44 1.4005(18) . ?
C44 H44 0.9500 . ?
C44 C45 1.381(2) . ?
C45 H45 0.9500 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C30 C31 C32 -176.36(12) . . . . ?
O1 C33 C34 N5 -145.15(12) . . . . ?
O1 C33 C34 C35 35.42(18) . . . . ?
O2 C40 C41 C42 -179.37(12) . . . . ?
O2 C40 C45 C44 178.70(12) . . . . ?
N1 C1 C2 C3 -0.34(15) . . . . ?
N1 C1 C20 C19 -14.54(17) . . . . ?
N1 C1 C20 C26 -134.22(13) . . . . ?
N1 C1 C20 C43 106.25(14) . . . . ?
N1 C4 C5 C6 -30.81(17) . . . . ?
N1 C4 C5 C21 88.79(15) . . . . ?
N1 C4 C5 C22 -152.30(12) . . . . ?
N2 C6 C7 C8 0.21(15) . . . . ?
N2 C9 C10 C11 105.20(14) . . . . ?
N2 C9 C10 C23 -136.44(13) . . . . ?
N2 C9 C10 C27 -12.85(17) . . . . ?
N3 C11 C12 C13 -0.56(16) . . . . ?
N3 C14 C15 C16 -37.14(18) . . . . ?
N3 C14 C15 C24 83.45(18) . . . . ?
N3 C14 C15 C25 -157.37(13) . . . . ?
N4 C16 C17 C18 -0.56(15) . . . . ?
N4 C19 C20 C1 95.02(14) . . . . ?
N4 C19 C20 C26 -146.29(12) . . . . ?
N4 C19 C20 C43 -27.14(16) . . . . ?
N5 C34 C35 C36 0.1(2) . . . . ?
N5 C38 C39 O2 114.90(13) . . . . ?
C1 N1 C4 C3 0.68(15) . . . . ?
C1 N1 C4 C5 -173.34(11) . . . . ?
C1 C2 C3 C4 0.76(15) . . . . ?
C1 C20 C43 C42 -5.25(17) . . . . ?
C1 C20 C43 C44 175.29(11) . . . . ?
C2 C1 C20 C19 173.04(13) . . . . ?
C2 C1 C20 C26 53.36(18) . . . . ?
C2 C1 C20 C43 -66.17(18) . . . . ?
C2 C3 C4 N1 -0.87(15) . . . . ?
C2 C3 C4 C5 172.43(13) . . . . ?
C3 C4 C5 C6 156.77(14) . . . . ?
C3 C4 C5 C21 -83.63(18) . . . . ?
C3 C4 C5 C22 35.27(19) . . . . ?
C4 N1 C1 C2 -0.20(15) . . . . ?
C4 N1 C1 C20 -174.13(11) . . . . ?
C4 C5 C6 N2 -59.10(16) . . . . ?
C4 C5 C6 C7 118.72(16) . . . . ?
C5 C6 C7 C8 -177.85(13) . . . . ?
C6 N2 C9 C8 -0.07(15) . . . . ?
C6 N2 C9 C10 -176.69(11) . . . . ?
C6 C7 C8 C9 -0.26(16) . . . . ?
C7 C8 C9 N2 0.20(15) . . . . ?
C7 C8 C9 C10 176.49(13) . . . . ?
C8 C9 C10 C11 -70.57(18) . . . . ?
C8 C9 C10 C23 47.79(19) . . . . ?
C8 C9 C10 C27 171.38(14) . . . . ?
C9 N2 C6 C5 178.23(11) . . . . ?
C9 N2 C6 C7 -0.10(15) . . . . ?
C9 C10 C11 N3 -5.28(17) . . . . ?
C9 C10 C11 C12 -177.69(14) . . . . ?
C9 C10 C27 C28 -109.82(14) . . . . ?
C9 C10 C27 C32 72.86(15) . . . . ?
C10 C11 C12 C13 172.75(13) . . . . ?
C10 C27 C28 C29 -175.08(13) . . . . ?
C10 C27 C32 C31 176.20(12) . . . . ?
C11 N3 C14 C13 -0.52(15) . . . . ?
C11 N3 C14 C15 -177.09(12) . . . . ?
C11 C10 C27 C28 130.60(13) . . . . ?
C11 C10 C27 C32 -46.71(15) . . . . ?
C11 C12 C13 C14 0.26(17) . . . . ?
C12 C13 C14 N3 0.16(16) . . . . ?
C12 C13 C14 C15 176.23(14) . . . . ?
C13 C14 C15 C16 147.26(15) . . . . ?
C13 C14 C15 C24 -92.1(2) . . . . ?
C13 C14 C15 C25 27.0(2) . . . . ?
C14 N3 C11 C10 -173.24(12) . . . . ?
C14 N3 C11 C12 0.68(15) . . . . ?
C14 C15 C16 N4 -48.95(18) . . . . ?
C14 C15 C16 C17 136.40(16) . . . . ?
C15 C16 C17 C18 174.68(14) . . . . ?
C16 N4 C19 C18 -0.82(15) . . . . ?
C16 N4 C19 C20 -178.92(11) . . . . ?
C16 C17 C18 C19 0.08(16) . . . . ?
C17 C18 C19 N4 0.44(15) . . . . ?
C17 C18 C19 C20 178.29(13) . . . . ?
C18 C19 C20 C1 -82.56(17) . . . . ?
C18 C19 C20 C26 36.14(19) . . . . ?
C18 C19 C20 C43 155.29(14) . . . . ?
C19 N4 C16 C15 -175.01(12) . . . . ?
C19 N4 C16 C17 0.87(15) . . . . ?
C19 C20 C43 C42 117.01(13) . . . . ?
C19 C20 C43 C44 -62.45(14) . . . . ?
C20 C1 C2 C3 173.02(13) . . . . ?
C20 C43 C44 C45 -179.00(12) . . . . ?
C21 C5 C6 N2 -178.55(12) . . . . ?
C21 C5 C6 C7 -0.7(2) . . . . ?
C22 C5 C6 N2 62.05(16) . . . . ?
C22 C5 C6 C7 -120.12(16) . . . . ?
C23 C10 C11 N3 -123.34(13) . . . . ?
C23 C10 C11 C12 64.24(18) . . . . ?
C23 C10 C27 C28 11.47(18) . . . . ?
C23 C10 C27 C32 -165.84(12) . . . . ?
C24 C15 C16 N4 -169.88(13) . . . . ?
C24 C15 C16 C17 15.5(2) . . . . ?
C25 C15 C16 N4 71.03(17) . . . . ?
C25 C15 C16 C17 -103.62(19) . . . . ?
C26 C20 C43 C42 -123.81(13) . . . . ?
C26 C20 C43 C44 56.72(16) . . . . ?
C27 C10 C11 N3 115.29(13) . . . . ?
C27 C10 C11 C12 -57.12(18) . . . . ?
C27 C28 C29 C30 -0.7(2) . . . . ?
C28 C27 C32 C31 -1.3(2) . . . . ?
C28 C29 C30 O1 177.40(13) . . . . ?
C28 C29 C30 C31 -2.0(2) . . . . ?
C29 C30 C31 C32 2.9(2) . . . . ?
C30 O1 C33 C34 74.31(15) . . . . ?
C30 C31 C32 C27 -1.3(2) . . . . ?
C32 C27 C28 C29 2.3(2) . . . . ?
C33 O1 C30 C29 170.60(12) . . . . ?
C33 O1 C30 C31 -10.08(19) . . . . ?
C33 C34 C35 C36 179.46(12) . . . . ?
C34 N5 C38 C37 0.90(19) . . . . ?
C34 N5 C38 C39 -178.44(12) . . . . ?
C34 C35 C36 C37 0.6(2) . . . . ?
C35 C36 C37 C38 -0.5(2) . . . . ?
C36 C37 C38 N5 -0.2(2) . . . . ?
C36 C37 C38 C39 179.10(12) . . . . ?
C37 C38 C39 O2 -64.46(16) . . . . ?
C38 N5 C34 C33 179.74(11) . . . . ?
C38 N5 C34 C35 -0.83(19) . . . . ?
C39 O2 C40 C41 13.56(19) . . . . ?
C39 O2 C40 C45 -166.54(12) . . . . ?
C40 O2 C39 C38 -84.00(14) . . . . ?
C40 C41 C42 C43 1.10(19) . . . . ?
C41 C40 C45 C44 -1.40(19) . . . . ?
C41 C42 C43 C20 178.34(12) . . . . ?
C41 C42 C43 C44 -2.19(19) . . . . ?
C42 C43 C44 C45 1.51(19) . . . . ?
C43 C44 C45 C40 0.3(2) . . . . ?
C45 C40 C41 C42 0.74(19) . . . . ?
