#------------------------------------------------------------------------------
#$Date: 2019-11-24 03:48:43 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236565 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/68/7236841.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_7236841
loop_
_publ_author_name
'Xie, Wen-Zhao'
'Zhang, Hong-Chao'
'Zheng, Yan-Song'
_publ_section_title
;
 Tetraphenylethylene tetracylhydrazine macrocycle with capability for
 discrimination of n-propanol from i-propanol and highly
 sensitive/selective detection of nitrobenzene
;
_journal_issue                   40
_journal_name_full               'J. Mater. Chem. C'
_journal_page_first              10462
_journal_paper_doi               10.1039/C7TC02525D
_journal_volume                  5
_journal_year                    2017
_chemical_formula_moiety         'C50 H48 N2 O4, C2 H6 O'
_chemical_formula_sum            'C52 H54 N2 O5'
_chemical_formula_weight         786.97
_chemical_melting_point          282.5(5)
_chemical_name_systematic        'TPEtetracylhydrazine macrocycle'
_chemical_properties_physical    ', Efflorescent'
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-06-05 deposited with the CCDC.
2017-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.749(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   38.906(10)
_cell_length_b                   9.493(2)
_cell_length_c                   27.486(7)
_cell_measurement_reflns_used    4630
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      25.46
_cell_measurement_theta_min      2.21
_cell_volume                     9901(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            40424
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         1.073
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0769 before and 0.0553 after correction.
The Ratio of minimum to maximum transmission is 0.7758.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.056
_exptl_crystal_description       block
_exptl_crystal_F_000             3360
_exptl_crystal_preparation       ', Luminescent'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform and ethanol'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         11291
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1386
_refine_ls_R_factor_gt           0.0838
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1651P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2378
_refine_ls_wR_factor_ref         0.2675
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6075
_reflns_number_total             11291
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7tc02525d2.cif
_cod_data_source_block           mo_dm15646_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '282-283' was changed to
'282.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               7236841
_shelxl_version_number           2014-3
_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_max   0.980
_shelx_estimated_absorpt_t_min   0.974
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
O4 \\sim C46 \\sim C47 \\sim C48 \\sim C49 \\sim C50: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C46(H46A,
 H46B), C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B), C51(H51A,H51B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12),
 C13(H13), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24),
  C25(H25), C30(H30), C31(H31), C33(H33), C34(H34), C41(H41), C42(H42),
 C44(H44), C45(H45)
3.c Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C50(H50A,H50B,H50C), C52(H52A,H52B,H52C)
3.d Idealised tetrahedral OH refined as rotating group:
 O5(H5A)
;
_olex2_submission_special_instructions 'No special instructions were received'
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_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
O1 O -0.03239(5) 0.1015(2) 0.43781(8) 0.0436(5) Uani 1 1 d . .
O2 O -0.01818(5) 0.3097(2) 0.12702(8) 0.0445(5) Uani 1 1 d . .
O3 O -0.20675(6) 0.9742(2) 0.15865(8) 0.0483(6) Uani 1 1 d . .
O4 O -0.19607(7) 0.3865(5) 0.44278(10) 0.1068(12) Uani 1 1 d . U
N1 N 0.01945(6) 0.0549(2) 0.41763(10) 0.0413(6) Uani 1 1 d . .
H1 H 0.0315 -0.0037 0.4030 0.050 Uiso 1 1 calc R .
N2 N -0.03611(6) 0.1735(2) 0.05812(10) 0.0414(6) Uani 1 1 d . .
H2 H -0.0477 0.1686 0.0268 0.050 Uiso 1 1 calc R .
C1 C -0.01425(7) 0.0290(3) 0.41629(10) 0.0328(6) Uani 1 1 d . .
C2 C -0.02840(7) -0.1016(2) 0.38744(10) 0.0304(6) Uani 1 1 d . .
C3 C -0.01136(7) -0.2303(3) 0.40144(11) 0.0363(6) Uani 1 1 d . .
H3 H 0.0096 -0.2323 0.4268 0.044 Uiso 1 1 calc R .
C4 C -0.02496(8) -0.3545(3) 0.37847(12) 0.0414(7) Uani 1 1 d . .
H4 H -0.0132 -0.4414 0.3877 0.050 Uiso 1 1 calc R .
C5 C -0.05541(8) -0.3510(3) 0.34244(11) 0.0393(7) Uani 1 1 d . .
H5 H -0.0650 -0.4364 0.3271 0.047 Uiso 1 1 calc R .
C6 C -0.07255(7) -0.2246(3) 0.32791(11) 0.0351(6) Uani 1 1 d . .
H6 H -0.0936 -0.2247 0.3027 0.042 Uiso 1 1 calc R .
C7 C -0.05921(7) -0.0970(3) 0.34983(10) 0.0297(6) Uani 1 1 d . .
C8 C -0.07641(7) 0.0374(3) 0.32917(10) 0.0297(6) Uani 1 1 d . .
C9 C -0.11286(7) 0.0520(3) 0.31852(11) 0.0342(6) Uani 1 1 d . .
H9 H -0.1269 -0.0210 0.3277 0.041 Uiso 1 1 calc R .
C10 C -0.12906(7) 0.1717(3) 0.29467(10) 0.0351(6) Uani 1 1 d . .
H10 H -0.1540 0.1807 0.2886 0.042 Uiso 1 1 calc R .
C11 C -0.10921(7) 0.2786(3) 0.27962(10) 0.0313(6) Uani 1 1 d . .
C12 C -0.07272(7) 0.2632(3) 0.29025(11) 0.0335(6) Uani 1 1 d . .
H12 H -0.0587 0.3345 0.2801 0.040 Uiso 1 1 calc R .
C13 C -0.05641(7) 0.1456(3) 0.31543(10) 0.0315(6) Uani 1 1 d . .
H13 H -0.0314 0.1392 0.3233 0.038 Uiso 1 1 calc R .
C14 C -0.12538(7) 0.4057(3) 0.25109(10) 0.0322(6) Uani 1 1 d . .
C15 C -0.11165(7) 0.4351(3) 0.20568(10) 0.0313(6) Uani 1 1 d . .
C16 C -0.09428(8) 0.5603(3) 0.19970(11) 0.0389(7) Uani 1 1 d . .
H16 H -0.0911 0.6296 0.2252 0.047 Uiso 1 1 calc R .
C17 C -0.08158(8) 0.5854(3) 0.15732(11) 0.0383(7) Uani 1 1 d . .
H17 H -0.0705 0.6728 0.1539 0.046 Uiso 1 1 calc R .
C18 C -0.08472(7) 0.4851(3) 0.11954(10) 0.0316(6) Uani 1 1 d . .
C19 C -0.10173(8) 0.3597(3) 0.12560(11) 0.0372(6) Uani 1 1 d . .
H19 H -0.1043 0.2892 0.1005 0.045 Uiso 1 1 calc R .
C20 C -0.11494(8) 0.3360(3) 0.16755(11) 0.0370(6) Uani 1 1 d . .
H20 H -0.1266 0.2496 0.1705 0.044 Uiso 1 1 calc R .
C21 C -0.07190(7) 0.5151(3) 0.07338(10) 0.0306(6) Uani 1 1 d . .
C22 C -0.08175(7) 0.6402(3) 0.04770(11) 0.0361(6) Uani 1 1 d . .
H22 H -0.0958 0.7060 0.0608 0.043 Uiso 1 1 calc R .
C23 C -0.07176(7) 0.6717(3) 0.00376(11) 0.0398(7) Uani 1 1 d . .
H23 H -0.0780 0.7595 -0.0123 0.048 Uiso 1 1 calc R .
C24 C -0.05249(8) 0.5741(3) -0.01668(12) 0.0420(7) Uani 1 1 d . .
H24 H -0.0463 0.5930 -0.0476 0.050 Uiso 1 1 calc R .
C25 C -0.04227(7) 0.4487(3) 0.00822(11) 0.0372(6) Uani 1 1 d . .
H25 H -0.0290 0.3820 -0.0057 0.045 Uiso 1 1 calc R .
C26 C -0.05129(7) 0.4195(3) 0.05351(10) 0.0317(6) Uani 1 1 d . .
C27 C -0.03417(7) 0.2970(3) 0.08363(11) 0.0349(6) Uani 1 1 d . .
C28 C -0.14950(7) 0.4873(3) 0.26598(11) 0.0357(6) Uani 1 1 d . .
C29 C -0.16632(7) 0.6122(3) 0.23724(10) 0.0344(6) Uani 1 1 d . .
C30 C -0.17739(8) 0.6156(3) 0.18559(11) 0.0406(7) Uani 1 1 d . .
H30 H -0.1750 0.5331 0.1670 0.049 Uiso 1 1 calc R .
C31 C -0.19162(8) 0.7345(3) 0.16059(12) 0.0446(7) Uani 1 1 d . .
H31 H -0.1997 0.7323 0.1254 0.054 Uiso 1 1 calc R .
C32 C -0.19423(7) 0.8591(3) 0.18692(11) 0.0377(6) Uani 1 1 d . .
C33 C -0.18475(7) 0.8575(3) 0.23806(12) 0.0399(7) Uani 1 1 d . .
H33 H -0.1874 0.9400 0.2565 0.048 Uiso 1 1 calc R .
C34 C -0.17122(7) 0.7347(3) 0.26305(12) 0.0378(6) Uani 1 1 d . .
H34 H -0.1652 0.7344 0.2985 0.045 Uiso 1 1 calc R .
C35 C -0.21428(9) 1.0987(3) 0.18368(13) 0.0492(8) Uani 1 1 d . .
H35A H -0.1922 1.1383 0.2041 0.059 Uiso 1 1 calc R .
H35B H -0.2303 1.0761 0.2060 0.059 Uiso 1 1 calc R .
C36 C -0.23131(10) 1.2034(4) 0.14495(15) 0.0609(9) Uani 1 1 d . .
H36A H -0.2498 1.1549 0.1201 0.073 Uiso 1 1 calc R .
H36B H -0.2134 1.2387 0.1274 0.073 Uiso 1 1 calc R .
C37 C -0.24771(11) 1.3277(4) 0.16572(17) 0.0678(11) Uani 1 1 d . .
H37A H -0.2652 1.2922 0.1841 0.081 Uiso 1 1 calc R .
H37B H -0.2291 1.3777 0.1899 0.081 Uiso 1 1 calc R .
C38 C -0.26552(15) 1.4304(5) 0.1273(2) 0.0979(17) Uani 1 1 d . .
H38A H -0.2475 1.4729 0.1115 0.117 Uiso 1 1 calc R .
H38B H -0.2822 1.3779 0.1011 0.117 Uiso 1 1 calc R .
C39 C -0.28491(17) 1.5444(6) 0.1452(3) 0.121(2) Uani 1 1 d . .
H39A H -0.2939 1.6101 0.1179 0.181 Uiso 1 1 calc GR .
H39B H -0.2691 1.5946 0.1724 0.181 Uiso 1 1 calc GR .
H39C H -0.3047 1.5049 0.1574 0.181 Uiso 1 1 calc GR .
C40 C -0.16061(7) 0.4612(3) 0.31388(11) 0.0373(6) Uani 1 1 d . .
C41 C -0.19573(8) 0.4400(3) 0.31369(12) 0.0457(7) Uani 1 1 d . .
H41 H -0.2127 0.4437 0.2830 0.055 Uiso 1 1 calc R .
C42 C -0.20660(9) 0.4137(4) 0.35706(13) 0.0567(9) Uani 1 1 d . .
H42 H -0.2308 0.3955 0.3560 0.068 Uiso 1 1 calc R .
C43 C -0.18260(9) 0.4136(4) 0.40224(13) 0.0598(9) Uani 1 1 d . .
C44 C -0.14757(9) 0.4367(4) 0.40310(13) 0.0612(10) Uani 1 1 d . .
H44 H -0.1307 0.4364 0.4339 0.073 Uiso 1 1 calc R .
C45 C -0.13699(8) 0.4600(4) 0.35936(12) 0.0476(8) Uani 1 1 d . .
H45 H -0.1127 0.4759 0.3604 0.057 Uiso 1 1 calc R .
C46 C -0.17269(16) 0.3905(9) 0.49042(18) 0.1345(17) Uani 1 1 d . U
H46A H -0.1611 0.4838 0.4960 0.161 Uiso 1 1 calc R .
H46B H -0.1542 0.3176 0.4926 0.161 Uiso 1 1 calc R .
C47 C -0.1935(2) 0.3642(10) 0.5282(2) 0.160(2) Uani 1 1 d . U
H47A H -0.2151 0.4229 0.5218 0.192 Uiso 1 1 calc R .
H47B H -0.1795 0.3849 0.5621 0.192 Uiso 1 1 calc R .
C48 C -0.2030(3) 0.2047(12) 0.5225(3) 0.191(2) Uani 1 1 d . U
H48A H -0.2216 0.1850 0.5411 0.229 Uiso 1 1 calc R .
H48B H -0.2130 0.1847 0.4869 0.229 Uiso 1 1 calc R .
C49 C -0.1723(3) 0.1036(14) 0.5411(4) 0.224(3) Uani 1 1 d . U
H49A H -0.1599 0.1241 0.5759 0.269 Uiso 1 1 calc R .
H49B H -0.1551 0.1043 0.5193 0.269 Uiso 1 1 calc R .
C50 C -0.1962(4) -0.0563(15) 0.5363(5) 0.279(5) Uani 1 1 d . U
H50A H -0.1826 -0.1314 0.5249 0.418 Uiso 1 1 calc GR .
H50B H -0.2188 -0.0449 0.5124 0.418 Uiso 1 1 calc GR .
H50C H -0.2006 -0.0812 0.5691 0.418 Uiso 1 1 calc GR .
O5 O 0.08038(6) 0.9415(3) 0.02573(9) 0.0606(7) Uani 1 1 d . .
H5A H 0.0695 0.9906 0.0428 0.091 Uiso 1 1 calc GR .
C51 C 0.11107(14) 0.8901(10) 0.05608(19) 0.147(3) Uani 1 1 d . .
H51A H 0.1052 0.8501 0.0865 0.177 Uiso 1 1 calc R .
H51B H 0.1274 0.9701 0.0665 0.177 Uiso 1 1 calc R .
C52 C 0.12860(17) 0.7879(8) 0.0346(4) 0.181(4) Uani 1 1 d . .
H52A H 0.1363 0.8283 0.0060 0.271 Uiso 1 1 calc GR .
H52B H 0.1127 0.7086 0.0234 0.271 Uiso 1 1 calc GR .
H52C H 0.1492 0.7547 0.0592 0.271 Uiso 1 1 calc GR .
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'
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
C32 O3 C35 118.2(2) . .
C43 O4 C46 117.9(3) . .
N2 N1 H1 119.5 2 .
C1 N1 H1 119.5 . .
C1 N1 N2 121.1(2) . 2
N1 N2 H2 120.6 2 .
C27 N2 N1 118.9(2) . 2
C27 N2 H2 120.6 . .
O1 C1 N1 123.5(3) . .
O1 C1 C2 122.2(2) . .
N1 C1 C2 114.3(2) . .
C3 C2 C1 118.4(2) . .
C7 C2 C1 121.1(2) . .
C7 C2 C3 120.3(2) . .
C2 C3 H3 119.8 . .
C4 C3 C2 120.4(3) . .
C4 C3 H3 119.8 . .
C3 C4 H4 120.3 . .
C5 C4 C3 119.5(3) . .
C5 C4 H4 120.3 . .
C4 C5 H5 119.5 . .
C4 C5 C6 120.9(3) . .
C6 C5 H5 119.5 . .
C5 C6 H6 119.5 . .
C5 C6 C7 121.0(3) . .
C7 C6 H6 119.5 . .
C2 C7 C6 117.8(2) . .
C2 C7 C8 123.1(2) . .
C6 C7 C8 118.9(2) . .
C9 C8 C7 121.1(2) . .
C13 C8 C7 120.3(2) . .
C13 C8 C9 118.4(2) . .
C8 C9 H9 119.5 . .
C8 C9 C10 121.0(2) . .
C10 C9 H9 119.5 . .
C9 C10 H10 119.6 . .
C11 C10 C9 120.8(2) . .
C11 C10 H10 119.6 . .
C10 C11 C12 117.9(2) . .
C10 C11 C14 123.1(2) . .
C12 C11 C14 119.0(2) . .
C11 C12 H12 119.3 . .
C13 C12 C11 121.4(2) . .
C13 C12 H12 119.3 . .
C8 C13 C12 120.5(2) . .
C8 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
C15 C14 C11 113.7(2) . .
C28 C14 C11 122.9(3) . .
C28 C14 C15 123.3(2) . .
C16 C15 C14 122.1(2) . .
C20 C15 C14 120.9(2) . .
C20 C15 C16 116.9(3) . .
C15 C16 H16 119.4 . .
C17 C16 C15 121.2(3) . .
C17 C16 H16 119.4 . .
C16 C17 H17 119.3 . .
C16 C17 C18 121.4(2) . .
C18 C17 H17 119.3 . .
C17 C18 C21 120.9(2) . .
C19 C18 C17 117.5(3) . .
C19 C18 C21 121.5(2) . .
C18 C19 H19 119.5 . .
C20 C19 C18 121.0(3) . .
C20 C19 H19 119.5 . .
C15 C20 H20 119.0 . .
C19 C20 C15 121.9(3) . .
C19 C20 H20 119.0 . .
C22 C21 C18 119.2(2) . .
C22 C21 C26 118.2(2) . .
C26 C21 C18 122.5(2) . .
C21 C22 H22 119.0 . .
C23 C22 C21 121.9(3) . .
C23 C22 H22 119.0 . .
C22 C23 H23 120.3 . .
C22 C23 C24 119.5(3) . .
C24 C23 H23 120.3 . .
C23 C24 H24 120.1 . .
C25 C24 C23 119.7(3) . .
C25 C24 H24 120.1 . .
C24 C25 H25 119.7 . .
C24 C25 C26 120.6(3) . .
C26 C25 H25 119.7 . .
C21 C26 C27 120.8(2) . .
C25 C26 C21 119.9(2) . .
C25 C26 C27 118.6(2) . .
O2 C27 N2 123.1(2) . .
O2 C27 C26 122.1(2) . .
N2 C27 C26 114.7(2) . .
C14 C28 C29 123.3(3) . .
C14 C28 C40 121.9(2) . .
C29 C28 C40 114.8(2) . .
C30 C29 C28 124.0(3) . .
C30 C29 C34 116.9(3) . .
C34 C29 C28 119.0(3) . .
C29 C30 H30 119.0 . .
C31 C30 C29 122.0(3) . .
C31 C30 H30 119.0 . .
C30 C31 H31 119.9 . .
C30 C31 C32 120.2(3) . .
C32 C31 H31 119.9 . .
O3 C32 C31 116.0(3) . .
O3 C32 C33 125.0(3) . .
C33 C32 C31 119.0(3) . .
C32 C33 H33 120.0 . .
C32 C33 C34 120.0(3) . .
C34 C33 H33 120.0 . .
C29 C34 H34 119.2 . .
C33 C34 C29 121.6(3) . .
C33 C34 H34 119.2 . .
O3 C35 H35A 110.1 . .
O3 C35 H35B 110.1 . .
O3 C35 C36 108.2(3) . .
H35A C35 H35B 108.4 . .
C36 C35 H35A 110.1 . .
C36 C35 H35B 110.1 . .
C35 C36 H36A 108.8 . .
C35 C36 H36B 108.8 . .
C35 C36 C37 114.0(3) . .
H36A C36 H36B 107.7 . .
C37 C36 H36A 108.8 . .
C37 C36 H36B 108.8 . .
C36 C37 H37A 108.7 . .
C36 C37 H37B 108.7 . .
H37A C37 H37B 107.6 . .
C38 C37 C36 114.3(4) . .
C38 C37 H37A 108.7 . .
C38 C37 H37B 108.7 . .
C37 C38 H38A 108.3 . .
C37 C38 H38B 108.3 . .
H38A C38 H38B 107.4 . .
C39 C38 C37 115.9(5) . .
C39 C38 H38A 108.3 . .
C39 C38 H38B 108.3 . .
C38 C39 H39A 109.5 . .
C38 C39 H39B 109.5 . .
C38 C39 H39C 109.5 . .
H39A C39 H39B 109.5 . .
H39A C39 H39C 109.5 . .
H39B C39 H39C 109.5 . .
C41 C40 C28 120.0(3) . .
C45 C40 C28 122.4(3) . .
C45 C40 C41 117.6(3) . .
C40 C41 H41 119.4 . .
C42 C41 C40 121.2(3) . .
C42 C41 H41 119.4 . .
C41 C42 H42 119.8 . .
C41 C42 C43 120.3(3) . .
C43 C42 H42 119.8 . .
O4 C43 C42 115.6(3) . .
O4 C43 C44 125.2(3) . .
C44 C43 C42 119.1(3) . .
C43 C44 H44 120.1 . .
C45 C44 C43 119.9(3) . .
C45 C44 H44 120.1 . .
C40 C45 H45 119.1 . .
C44 C45 C40 121.8(3) . .
C44 C45 H45 119.1 . .
O4 C46 H46A 110.1 . .
O4 C46 H46B 110.1 . .
O4 C46 C47 107.8(5) . .
H46A C46 H46B 108.5 . .
C47 C46 H46A 110.1 . .
C47 C46 H46B 110.1 . .
C46 C47 H47A 110.9 . .
C46 C47 H47B 110.9 . .
C46 C47 C48 104.5(7) . .
H47A C47 H47B 108.9 . .
C48 C47 H47A 110.9 . .
C48 C47 H47B 110.9 . .
C47 C48 H48A 108.5 . .
C47 C48 H48B 108.5 . .
H48A C48 H48B 107.5 . .
C49 C48 C47 115.1(9) . .
C49 C48 H48A 108.5 . .
C49 C48 H48B 108.5 . .
C48 C49 H49A 112.0 . .
C48 C49 H49B 112.0 . .
C48 C49 C50 98.8(10) . .
H49A C49 H49B 109.7 . .
C50 C49 H49A 112.0 . .
C50 C49 H49B 112.0 . .
C49 C50 H50A 109.5 . .
C49 C50 H50B 109.5 . .
C49 C50 H50C 109.5 . .
H50A C50 H50B 109.5 . .
H50A C50 H50C 109.5 . .
H50B C50 H50C 109.5 . .
C51 O5 H5A 109.5 . .
O5 C51 H51A 108.4 . .
O5 C51 H51B 108.4 . .
O5 C51 C52 115.3(5) . .
H51A C51 H51B 107.5 . .
C52 C51 H51A 108.4 . .
C52 C51 H51B 108.4 . .
C51 C52 H52A 109.5 . .
C51 C52 H52B 109.5 . .
C51 C52 H52C 109.5 . .
H52A C52 H52B 109.5 . .
H52A C52 H52C 109.5 . .
H52B C52 H52C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.227(3) .
O2 C27 1.223(3) .
O3 C32 1.366(3) .
O3 C35 1.430(4) .
O4 C43 1.356(4) .
O4 C46 1.420(6) .
N1 H1 0.8800 .
N1 N2 1.393(3) 2
N1 C1 1.327(4) .
N2 N1 1.393(3) 2
N2 H2 0.8800 .
N2 C27 1.359(4) .
C1 C2 1.508(4) .
C2 C3 1.403(3) .
C2 C7 1.400(4) .
C3 H3 0.9500 .
C3 C4 1.386(4) .
C4 H4 0.9500 .
C4 C5 1.367(4) .
C5 H5 0.9500 .
C5 C6 1.388(4) .
C6 H6 0.9500 .
C6 C7 1.401(4) .
C7 C8 1.493(3) .
C8 C9 1.390(4) .
C8 C13 1.390(4) .
C9 H9 0.9500 .
C9 C10 1.392(4) .
C10 H10 0.9500 .
C10 C11 1.392(4) .
C11 C12 1.392(4) .
C11 C14 1.500(4) .
C12 H12 0.9500 .
C12 C13 1.391(4) .
C13 H13 0.9500 .
C14 C15 1.488(4) .
C14 C28 1.348(4) .
C15 C16 1.395(4) .
C15 C20 1.393(4) .
C16 H16 0.9500 .
C16 C17 1.383(4) .
C17 H17 0.9500 .
C17 C18 1.394(4) .
C18 C19 1.390(4) .
C18 C21 1.490(4) .
C19 H19 0.9500 .
C19 C20 1.380(4) .
C20 H20 0.9500 .
C21 C22 1.392(4) .
C21 C26 1.399(4) .
C22 H22 0.9500 .
C22 C23 1.381(4) .
C23 H23 0.9500 .
C23 C24 1.386(4) .
C24 H24 0.9500 .
C24 C25 1.387(4) .
C25 H25 0.9500 .
C25 C26 1.394(4) .
C26 C27 1.496(4) .
C28 C29 1.493(4) .
C28 C40 1.494(4) .
C29 C30 1.390(4) .
C29 C34 1.397(4) .
C30 H30 0.9500 .
C30 C31 1.373(4) .
C31 H31 0.9500 .
C31 C32 1.402(4) .
C32 C33 1.372(4) .
C33 H33 0.9500 .
C33 C34 1.396(4) .
C34 H34 0.9500 .
C35 H35A 0.9900 .
C35 H35B 0.9900 .
C35 C36 1.500(5) .
C36 H36A 0.9900 .
C36 H36B 0.9900 .
C36 C37 1.512(5) .
C37 H37A 0.9900 .
C37 H37B 0.9900 .
C37 C38 1.491(6) .
C38 H38A 0.9900 .
C38 H38B 0.9900 .
C38 C39 1.466(6) .
C39 H39A 0.9800 .
C39 H39B 0.9800 .
C39 H39C 0.9800 .
C40 C41 1.380(4) .
C40 C45 1.378(4) .
C41 H41 0.9500 .
C41 C42 1.373(5) .
C42 H42 0.9500 .
C42 C43 1.379(5) .
C43 C44 1.375(5) .
C44 H44 0.9500 .
C44 C45 1.372(5) .
C45 H45 0.9500 .
C46 H46A 0.9900 .
C46 H46B 0.9900 .
C46 C47 1.472(8) .
C47 H47A 0.9900 .
C47 H47B 0.9900 .
C47 C48 1.558(12) .
C48 H48A 0.9900 .
C48 H48B 0.9900 .
C48 C49 1.531(14) .
C49 H49A 0.9900 .
C49 H49B 0.9900 .
C49 C50 1.771(15) .
C50 H50A 0.9800 .
C50 H50B 0.9800 .
C50 H50C 0.9800 .
O5 H5A 0.8400 .
O5 C51 1.386(6) .
C51 H51A 0.9900 .
C51 H51B 0.9900 .
C51 C52 1.391(9) .
C52 H52A 0.9800 .
C52 H52B 0.9800 .
C52 H52C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O5 0.88 2.00 2.778(3) 147.4 5_565
O5 H5A O1 0.84 1.95 2.761(3) 161.2 2_565
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
O1 C1 C2 C3 -121.6(3) .
O1 C1 C2 C7 54.0(4) .
O3 C32 C33 C34 -178.0(3) .
O3 C35 C36 C37 167.7(3) .
O4 C43 C44 C45 178.6(4) .
O4 C46 C47 C48 72.0(8) .
N1 N2 C27 O2 0.6(4) 2
N1 N2 C27 C26 176.9(2) 2
N1 C1 C2 C3 56.2(3) .
N1 C1 C2 C7 -128.2(3) .
N2 N1 C1 O1 -3.7(4) 2
N2 N1 C1 C2 178.5(2) 2
C1 C2 C3 C4 175.2(3) .
C1 C2 C7 C6 -174.1(2) .
C1 C2 C7 C8 11.5(4) .
C2 C3 C4 C5 -0.8(4) .
C2 C7 C8 C9 -139.3(3) .
C2 C7 C8 C13 47.3(4) .
C3 C2 C7 C6 1.4(4) .
C3 C2 C7 C8 -172.9(2) .
C3 C4 C5 C6 1.2(4) .
C4 C5 C6 C7 -0.2(4) .
C5 C6 C7 C2 -1.1(4) .
C5 C6 C7 C8 173.5(3) .
C6 C7 C8 C9 46.4(4) .
C6 C7 C8 C13 -127.0(3) .
C7 C2 C3 C4 -0.5(4) .
C7 C8 C9 C10 -173.5(3) .
C7 C8 C13 C12 171.6(2) .
C8 C9 C10 C11 1.8(4) .
C9 C8 C13 C12 -2.0(4) .
C9 C10 C11 C12 -1.5(4) .
C9 C10 C11 C14 176.2(3) .
C10 C11 C12 C13 -0.5(4) .
C10 C11 C14 C15 -129.9(3) .
C10 C11 C14 C28 51.6(4) .
C11 C12 C13 C8 2.3(4) .
C11 C14 C15 C16 -118.9(3) .
C11 C14 C15 C20 59.5(3) .
C11 C14 C28 C29 -178.6(2) .
C11 C14 C28 C40 3.3(4) .
C12 C11 C14 C15 47.8(3) .
C12 C11 C14 C28 -130.7(3) .
C13 C8 C9 C10 0.0(4) .
C14 C11 C12 C13 -178.3(2) .
C14 C15 C16 C17 179.7(3) .
C14 C15 C20 C19 -178.5(3) .
C14 C28 C29 C30 40.8(4) .
C14 C28 C29 C34 -138.6(3) .
C14 C28 C40 C41 -123.5(3) .
C14 C28 C40 C45 57.9(4) .
C15 C14 C28 C29 3.0(4) .
C15 C14 C28 C40 -175.1(2) .
C15 C16 C17 C18 -1.8(4) .
C16 C15 C20 C19 0.0(4) .
C16 C17 C18 C19 1.2(4) .
C16 C17 C18 C21 178.1(3) .
C17 C18 C19 C20 0.0(4) .
C17 C18 C21 C22 -49.4(4) .
C17 C18 C21 C26 133.0(3) .
C18 C19 C20 C15 -0.6(4) .
C18 C21 C22 C23 -177.7(3) .
C18 C21 C26 C25 175.2(2) .
C18 C21 C26 C27 -14.1(4) .
C19 C18 C21 C22 127.4(3) .
C19 C18 C21 C26 -50.1(4) .
C20 C15 C16 C17 1.2(4) .
C21 C18 C19 C20 -176.9(3) .
C21 C22 C23 C24 2.5(4) .
C21 C26 C27 O2 -46.2(4) .
C21 C26 C27 N2 137.5(3) .
C22 C21 C26 C25 -2.4(4) .
C22 C21 C26 C27 168.3(2) .
C22 C23 C24 C25 -2.6(4) .
C23 C24 C25 C26 0.2(4) .
C24 C25 C26 C21 2.3(4) .
C24 C25 C26 C27 -168.6(3) .
C25 C26 C27 O2 124.6(3) .
C25 C26 C27 N2 -51.7(3) .
C26 C21 C22 C23 0.0(4) .
C28 C14 C15 C16 59.6(4) .
C28 C14 C15 C20 -122.0(3) .
C28 C29 C30 C31 -177.7(3) .
C28 C29 C34 C33 175.9(2) .
C28 C40 C41 C42 179.0(3) .
C28 C40 C45 C44 179.6(3) .
C29 C28 C40 C41 58.2(4) .
C29 C28 C40 C45 -120.4(3) .
C29 C30 C31 C32 2.3(5) .
C30 C29 C34 C33 -3.5(4) .
C30 C31 C32 O3 176.2(3) .
C30 C31 C32 C33 -4.6(4) .
C31 C32 C33 C34 2.9(4) .
C32 O3 C35 C36 -173.7(3) .
C32 C33 C34 C29 1.3(4) .
C34 C29 C30 C31 1.7(4) .
C35 O3 C32 C31 172.0(3) .
C35 O3 C32 C33 -7.2(4) .
C35 C36 C37 C38 -178.5(4) .
C36 C37 C38 C39 173.8(5) .
C40 C28 C29 C30 -141.0(3) .
C40 C28 C29 C34 39.6(4) .
C40 C41 C42 C43 2.6(6) .
C41 C40 C45 C44 1.0(5) .
C41 C42 C43 O4 180.0(4) .
C41 C42 C43 C44 -1.6(6) .
C42 C43 C44 C45 0.3(6) .
C43 O4 C46 C47 177.5(6) .
C43 C44 C45 C40 0.0(6) .
C45 C40 C41 C42 -2.3(5) .
C46 O4 C43 C42 -177.6(5) .
C46 O4 C43 C44 4.1(8) .
C46 C47 C48 C49 71.6(9) .
C47 C48 C49 C50 171.5(7) .
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
1 0.000 -0.180 0.250 313.5 72.6
2 0.000 -0.106 0.750 313.5 72.6
3 0.250 0.250 0.500 75.6 16.7
4 0.250 0.750 0.000 75.6 16.7
5 0.500 0.315 0.750 313.5 72.6
6 0.500 -0.652 0.250 313.5 72.6
7 0.750 0.250 0.000 75.6 16.7
8 0.750 0.750 0.500 75.6 16.7
