#------------------------------------------------------------------------------
#$Date: 2019-11-24 02:12:21 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236202 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/39/1553957.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_1553957
loop_
_publ_author_name
'Krishnan, Jagadeesh'
'Jose, Anu'
'Sasidhar, B. S.'
'Suresh, E.'
'Menon, Rajeev S.'
'Nair, Vijay'
_publ_section_title
;
 An uncommon multicomponent reaction involving nucleophilic heterocyclic
 carbenes: facile synthesis of fully substituted cyclopentanones
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1202
_journal_paper_doi               10.1039/C7QO01051F
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C50.5 H49 Cl I N3 O5'
_chemical_formula_weight         940.28
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-08-10 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 124.203(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.069(3)
_cell_length_b                   16.6470(18)
_cell_length_c                   23.834(3)
_cell_measurement_reflns_used    5294
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.01
_cell_measurement_theta_min      2.46
_cell_volume                     9538.8(19)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFARCTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            28275
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  0.8993
_exptl_absorpt_correction_T_min  0.7896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCKS
_exptl_crystal_F_000             3864
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_platon_squeeze_details          ' ?'
_refine_diff_density_max         0.897
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         11068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0494P)²+5.5501P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0913
_reflns_number_gt                9292
_reflns_number_total             11068
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo01051f2.cif
_cod_data_source_block           jdk851xm
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

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

data item '_symmetry_cell_setting' value 'MONOCLINIC' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/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_cell_volume        9538.9(18)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C50.50 H49 Cl I N3 O5'
_cod_database_code               1553957
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.02359(5) 0.69101(6) 0.32277(6) 0.0828(3) Uani 1 1 d .
C54 C 0.0000 0.6330(3) 0.2500 0.0704(14) Uani 1 2 d S
H54A H -0.0300 0.5986 0.2421 0.084 Uiso 0.50 1 calc PR
H54B H 0.0300 0.5986 0.2579 0.084 Uiso 0.50 1 calc PR
I1 I 0.030665(6) 0.470735(9) 0.408600(7) 0.03148(6) Uani 1 1 d .
O3 O 0.13742(6) 0.57944(9) 0.66991(7) 0.0289(3) Uani 1 1 d .
O2 O 0.16486(6) 0.29207(9) 0.67919(7) 0.0280(3) Uani 1 1 d .
N3 N 0.11517(7) 0.45597(9) 0.62415(8) 0.0217(3) Uani 1 1 d .
C37 C 0.16222(9) 0.51980(12) 0.57254(11) 0.0252(4) Uani 1 1 d .
O1 O 0.08818(7) 0.13388(10) 0.50879(8) 0.0390(4) Uani 1 1 d .
C30 C 0.12601(8) 0.50950(12) 0.67364(10) 0.0227(4) Uani 1 1 d .
C44 C -0.01682(8) 0.25659(11) 0.48819(10) 0.0233(4) Uani 1 1 d .
O5 O -0.17427(7) 0.18431(11) 0.43441(9) 0.0432(4) Uani 1 1 d .
N1 N 0.20988(8) 0.13090(12) 0.65066(9) 0.0338(4) Uani 1 1 d .
C38 C 0.20997(9) 0.47221(13) 0.60585(11) 0.0295(4) Uani 1 1 d .
H38 H 0.2100 0.4240 0.6256 0.035 Uiso 1 1 calc R
O4 O 0.30665(7) 0.58752(11) 0.58775(9) 0.0462(4) Uani 1 1 d .
C29 C 0.07994(8) 0.42592(12) 0.51070(10) 0.0226(4) Uani 1 1 d .
H29 H 0.1086 0.3904 0.5149 0.027 Uiso 1 1 calc R
C24 C 0.11962(8) 0.30204(12) 0.62404(10) 0.0234(4) Uani 1 1 d .
C27 C 0.03891(8) 0.28916(12) 0.50714(10) 0.0224(4) Uani 1 1 d .
H27 H 0.0407 0.2858 0.4674 0.027 Uiso 1 1 calc R
C31 C 0.12558(8) 0.48450(12) 0.73407(10) 0.0241(4) Uani 1 1 d .
N2 N 0.14843(8) 0.09888(11) 0.67112(9) 0.0325(4) Uani 1 1 d .
C23 C 0.09051(8) 0.25045(12) 0.56673(10) 0.0235(4) Uani 1 1 d .
C34 C 0.13189(10) 0.45646(15) 0.85321(12) 0.0365(5) Uani 1 1 d .
H34 H 0.1345 0.4471 0.8934 0.044 Uiso 1 1 calc R
C46 C -0.11652(9) 0.25017(14) 0.40419(11) 0.0314(5) Uani 1 1 d .
H46 H -0.1470 0.2622 0.3608 0.038 Uiso 1 1 calc R
C22 C 0.10846(8) 0.17461(12) 0.56127(10) 0.0268(4) Uani 1 1 d .
C32 C 0.14326(8) 0.41033(13) 0.76597(10) 0.0283(4) Uani 1 1 d .
H32 H 0.1532 0.3700 0.7477 0.034 Uiso 1 1 calc R
C26 C 0.04584(8) 0.37821(11) 0.52954(10) 0.0210(4) Uani 1 1 d .
H26 H 0.0100 0.4038 0.5128 0.025 Uiso 1 1 calc R
C35 C 0.11389(11) 0.53018(15) 0.82132(13) 0.0376(5) Uani 1 1 d .
H35 H 0.1036 0.5701 0.8396 0.045 Uiso 1 1 calc R
C36 C 0.11107(10) 0.54482(14) 0.76223(12) 0.0322(5) Uani 1 1 d .
H36 H 0.0995 0.5948 0.7413 0.039 Uiso 1 1 calc R
C41 C 0.21041(10) 0.61612(14) 0.54696(12) 0.0364(5) Uani 1 1 d .
H41 H 0.2103 0.6642 0.5271 0.044 Uiso 1 1 calc R
C48 C -0.07767(10) 0.19305(14) 0.51372(12) 0.0356(5) Uani 1 1 d .
H48 H -0.0822 0.1662 0.5445 0.043 Uiso 1 1 calc R
C45 C -0.06338(8) 0.27278(13) 0.42410(11) 0.0299(5) Uani 1 1 d .
H45 H -0.0589 0.2998 0.3933 0.036 Uiso 1 1 calc R
C33 C 0.14603(9) 0.39682(15) 0.82541(11) 0.0336(5) Uani 1 1 d .
H33 H 0.1576 0.3470 0.8466 0.040 Uiso 1 1 calc R
C39 C 0.25736(9) 0.49640(15) 0.60971(12) 0.0330(5) Uani 1 1 d .
H39 H 0.2891 0.4644 0.6319 0.040 Uiso 1 1 calc R
C47 C -0.12361(9) 0.20965(13) 0.44934(11) 0.0292(4) Uani 1 1 d .
C49 C -0.02491(9) 0.21606(14) 0.53287(11) 0.0311(5) Uani 1 1 d .
H49 H 0.0055 0.2042 0.5763 0.037 Uiso 1 1 calc R
C28 C 0.10886(8) 0.49287(12) 0.56332(10) 0.0232(4) Uani 1 1 d .
H28 H 0.0836 0.5389 0.5488 0.028 Uiso 1 1 calc R
C15 C 0.08126(10) 0.12193(13) 0.70101(12) 0.0336(5) Uani 1 1 d .
C40 C 0.25744(9) 0.56862(15) 0.58031(12) 0.0341(5) Uani 1 1 d .
C21 C 0.11778(12) 0.18519(16) 0.75175(13) 0.0443(6) Uani 1 1 d .
H21A H 0.1444 0.1602 0.7944 0.066 Uiso 1 1 calc R
H21B H 0.0953 0.2220 0.7575 0.066 Uiso 1 1 calc R
H21C H 0.1370 0.2138 0.7358 0.066 Uiso 1 1 calc R
C9 C 0.15562(9) 0.13634(13) 0.62691(11) 0.0287(4) Uani 1 1 d .
C12 C 0.01399(13) -0.00002(18) 0.61153(15) 0.0532(7) Uani 1 1 d .
H12 H -0.0084 -0.0409 0.5821 0.064 Uiso 1 1 calc R
C42 C 0.16315(10) 0.59116(13) 0.54346(12) 0.0325(5) Uani 1 1 d .
H42 H 0.1315 0.6232 0.5211 0.039 Uiso 1 1 calc R
C17 C 0.33327(12) 0.2081(2) 0.53703(15) 0.0616(9) Uani 1 1 d .
H17A H 0.3687 0.1818 0.5643 0.092 Uiso 1 1 calc R
H17B H 0.3388 0.2651 0.5382 0.092 Uiso 1 1 calc R
H17C H 0.3143 0.1894 0.4911 0.092 Uiso 1 1 calc R
C6 C 0.23783(9) 0.15455(15) 0.61858(11) 0.0348(5) Uani 1 1 d .
C18 C 0.19748(14) 0.02947(17) 0.54546(17) 0.0581(8) Uani 1 1 d .
H18A H 0.2014 0.0010 0.5133 0.087 Uiso 1 1 calc R
H18B H 0.1592 0.0441 0.5245 0.087 Uiso 1 1 calc R
H18C H 0.2093 -0.0044 0.5839 0.087 Uiso 1 1 calc R
C10 C 0.09582(10) 0.08073(14) 0.66235(12) 0.0340(5) Uani 1 1 d .
C8 C 0.19940(11) 0.07107(17) 0.72488(13) 0.0456(6) Uani 1 1 d .
H8 H 0.2060 0.0433 0.7626 0.055 Uiso 1 1 calc R
C14 C 0.03120(11) 0.10123(16) 0.69203(13) 0.0429(6) Uani 1 1 d .
H14 H 0.0202 0.1286 0.7166 0.051 Uiso 1 1 calc R
C11 C 0.06346(12) 0.01826(15) 0.61820(13) 0.0433(6) Uani 1 1 d .
C1 C 0.27374(9) 0.22001(16) 0.64426(11) 0.0371(5) Uani 1 1 d .
C5 C 0.23268(11) 0.10397(16) 0.56829(12) 0.0424(6) Uani 1 1 d .
C50 C -0.22032(10) 0.1925(2) 0.36603(14) 0.0565(8) Uani 1 1 d .
H50A H -0.2274 0.2484 0.3545 0.085 Uiso 1 1 calc R
H50B H -0.2526 0.1683 0.3606 0.085 Uiso 1 1 calc R
H50C H -0.2122 0.1662 0.3367 0.085 Uiso 1 1 calc R
C13 C -0.00300(12) 0.04088(17) 0.64750(15) 0.0501(7) Uani 1 1 d .
C2 C 0.30311(10) 0.23684(17) 0.61541(12) 0.0418(6) Uani 1 1 d .
H2 H 0.3265 0.2813 0.6306 0.050 Uiso 1 1 calc R
C19 C 0.08201(15) -0.03033(16) 0.58107(17) 0.0582(8) Uani 1 1 d .
H19A H 0.0812 0.0027 0.5475 0.087 Uiso 1 1 calc R
H19B H 0.0575 -0.0753 0.5593 0.087 Uiso 1 1 calc R
H19C H 0.1192 -0.0494 0.6127 0.087 Uiso 1 1 calc R
C3 C 0.29865(11) 0.18933(18) 0.56460(13) 0.0467(7) Uani 1 1 d .
C7 C 0.23736(11) 0.09152(17) 0.71261(13) 0.0461(6) Uani 1 1 d .
H7 H 0.2753 0.0812 0.7405 0.055 Uiso 1 1 calc R
C4 C 0.26351(11) 0.12428(18) 0.54219(13) 0.0479(7) Uani 1 1 d .
H4 H 0.2602 0.0924 0.5080 0.057 Uiso 1 1 calc R
C16 C 0.28377(10) 0.26911(18) 0.70342(13) 0.0456(6) Uani 1 1 d .
H16A H 0.3088 0.2408 0.7449 0.068 Uiso 1 1 calc R
H16B H 0.2491 0.2779 0.6987 0.068 Uiso 1 1 calc R
H16C H 0.2998 0.3199 0.7043 0.068 Uiso 1 1 calc R
C25 C 0.08442(8) 0.37940(11) 0.60724(10) 0.0212(4) Uani 1 1 d .
H25 H 0.0628 0.3772 0.6273 0.025 Uiso 1 1 calc R
C43 C 0.30799(13) 0.6608(2) 0.55786(17) 0.0608(8) Uani 1 1 d .
H43A H 0.2809 0.6589 0.5097 0.091 Uiso 1 1 calc R
H43B H 0.3443 0.6682 0.5669 0.091 Uiso 1 1 calc R
H43C H 0.2997 0.7048 0.5768 0.091 Uiso 1 1 calc R
C20 C -0.05682(15) 0.0196(2) 0.6401(2) 0.0752(11) Uani 1 1 d .
H20A H -0.0491 -0.0155 0.6763 0.113 Uiso 1 1 calc R
H20B H -0.0813 -0.0068 0.5974 0.113 Uiso 1 1 calc R
H20C H -0.0742 0.0678 0.6418 0.113 Uiso 1 1 calc R
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'
I I -0.4742 1.8119 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
Cl1 C54 Cl1 113.1(2) . 2
Cl1 C54 H54A 109.0 . .
Cl1 C54 H54A 109.0 2 .
Cl1 C54 H54B 109.0 . .
Cl1 C54 H54B 109.0 2 .
H54A C54 H54B 107.8 . .
C30 N3 C25 127.51(16) . .
C30 N3 C28 114.47(16) . .
C25 N3 C28 111.48(15) . .
C42 C37 C38 118.66(19) . .
C42 C37 C28 119.39(19) . .
C38 C37 C28 121.81(19) . .
O3 C30 N3 119.78(18) . .
O3 C30 C31 118.63(18) . .
N3 C30 C31 121.57(18) . .
C45 C44 C49 117.35(19) . .
C45 C44 C27 118.52(18) . .
C49 C44 C27 123.97(18) . .
C47 O5 C50 116.77(18) . .
C9 N1 C7 108.48(19) . .
C9 N1 C6 129.20(18) . .
C7 N1 C6 122.16(19) . .
C39 C38 C37 120.4(2) . .
C39 C38 H38 119.8 . .
C37 C38 H38 119.8 . .
C40 O4 C43 116.8(2) . .
C26 C29 C28 106.71(15) . .
C26 C29 I1 112.68(12) . .
C28 C29 I1 112.66(13) . .
C26 C29 H29 108.2 . .
C28 C29 H29 108.2 . .
I1 C29 H29 108.2 . .
O2 C24 C23 129.85(18) . .
O2 C24 C25 122.47(17) . .
C23 C24 C25 107.67(16) . .
C23 C27 C44 117.18(17) . .
C23 C27 C26 102.47(15) . .
C44 C27 C26 110.79(15) . .
C23 C27 H27 108.7 . .
C44 C27 H27 108.7 . .
C26 C27 H27 108.7 . .
C32 C31 C36 119.64(19) . .
C32 C31 C30 124.74(18) . .
C36 C31 C30 115.32(19) . .
C9 N2 C8 109.0(2) . .
C9 N2 C10 126.93(18) . .
C8 N2 C10 123.7(2) . .
C22 C23 C24 125.64(18) . .
C22 C23 C27 121.45(18) . .
C24 C23 C27 112.67(17) . .
C33 C34 C35 119.9(2) . .
C33 C34 H34 120.1 . .
C35 C34 H34 120.1 . .
C47 C46 C45 119.4(2) . .
C47 C46 H46 120.3 . .
C45 C46 H46 120.3 . .
O1 C22 C23 126.53(19) . .
O1 C22 C9 116.70(18) . .
C23 C22 C9 116.68(18) . .
C31 C32 C33 119.5(2) . .
C31 C32 H32 120.2 . .
C33 C32 H32 120.2 . .
C29 C26 C25 101.20(15) . .
C29 C26 C27 112.19(15) . .
C25 C26 C27 107.06(15) . .
C29 C26 H26 111.9 . .
C25 C26 H26 111.9 . .
C27 C26 H26 111.9 . .
C34 C35 C36 120.2(2) . .
C34 C35 H35 119.9 . .
C36 C35 H35 119.9 . .
C35 C36 C31 120.0(2) . .
C35 C36 H36 120.0 . .
C31 C36 H36 120.0 . .
C40 C41 C42 119.2(2) . .
C40 C41 H41 120.4 . .
C42 C41 H41 120.4 . .
C47 C48 C49 120.7(2) . .
C47 C48 H48 119.7 . .
C49 C48 H48 119.7 . .
C44 C45 C46 122.3(2) . .
C44 C45 H45 118.9 . .
C46 C45 H45 118.9 . .
C34 C33 C32 120.7(2) . .
C34 C33 H33 119.6 . .
C32 C33 H33 119.6 . .
C38 C39 C40 120.0(2) . .
C38 C39 H39 120.0 . .
C40 C39 H39 120.0 . .
O5 C47 C46 123.8(2) . .
O5 C47 C48 116.9(2) . .
C46 C47 C48 119.27(19) . .
C48 C49 C44 121.0(2) . .
C48 C49 H49 119.5 . .
C44 C49 H49 119.5 . .
N3 C28 C37 115.32(16) . .
N3 C28 C29 102.01(15) . .
C37 C28 C29 112.51(16) . .
N3 C28 H28 108.9 . .
C37 C28 H28 108.9 . .
C29 C28 H28 108.9 . .
C14 C15 C10 117.2(2) . .
C14 C15 C21 120.2(2) . .
C10 C15 C21 122.6(2) . .
O4 C40 C41 124.4(2) . .
O4 C40 C39 115.4(2) . .
C41 C40 C39 120.2(2) . .
C15 C21 H21A 109.5 . .
C15 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C15 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
N2 C9 N1 107.59(18) . .
N2 C9 C22 123.70(19) . .
N1 C9 C22 128.7(2) . .
C13 C12 C11 121.9(3) . .
C13 C12 H12 119.1 . .
C11 C12 H12 119.1 . .
C37 C42 C41 121.5(2) . .
C37 C42 H42 119.2 . .
C41 C42 H42 119.2 . .
C3 C17 H17A 109.5 . .
C3 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C3 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C1 C6 C5 122.7(2) . .
C1 C6 N1 119.1(2) . .
C5 C6 N1 117.8(2) . .
C5 C18 H18A 109.5 . .
C5 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C5 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C15 C10 C11 122.5(2) . .
C15 C10 N2 119.3(2) . .
C11 C10 N2 118.0(2) . .
C7 C8 N2 107.4(2) . .
C7 C8 H8 126.3 . .
N2 C8 H8 126.3 . .
C15 C14 C13 122.2(2) . .
C15 C14 H14 118.9 . .
C13 C14 H14 118.9 . .
C12 C11 C10 117.6(2) . .
C12 C11 C19 120.3(3) . .
C10 C11 C19 122.0(3) . .
C6 C1 C2 117.2(2) . .
C6 C1 C16 122.6(2) . .
C2 C1 C16 120.1(2) . .
C4 C5 C6 116.8(3) . .
C4 C5 C18 121.2(2) . .
C6 C5 C18 122.0(2) . .
O5 C50 H50A 109.5 . .
O5 C50 H50B 109.5 . .
H50A C50 H50B 109.5 . .
O5 C50 H50C 109.5 . .
H50A C50 H50C 109.5 . .
H50B C50 H50C 109.5 . .
C12 C13 C14 118.5(3) . .
C12 C13 C20 121.2(3) . .
C14 C13 C20 120.4(3) . .
C3 C2 C1 122.2(3) . .
C3 C2 H2 118.9 . .
C1 C2 H2 118.9 . .
C11 C19 H19A 109.5 . .
C11 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C11 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C4 C3 C2 118.2(2) . .
C4 C3 C17 121.7(3) . .
C2 C3 C17 120.1(3) . .
C8 C7 N1 107.6(2) . .
C8 C7 H7 126.2 . .
N1 C7 H7 126.2 . .
C3 C4 C5 122.9(2) . .
C3 C4 H4 118.5 . .
C5 C4 H4 118.5 . .
C1 C16 H16A 109.5 . .
C1 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C1 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
N3 C25 C26 105.07(15) . .
N3 C25 C24 115.84(15) . .
C26 C25 C24 103.27(15) . .
N3 C25 H25 110.7 . .
C26 C25 H25 110.7 . .
C24 C25 H25 110.7 . .
O4 C43 H43A 109.5 . .
O4 C43 H43B 109.5 . .
H43A C43 H43B 109.5 . .
O4 C43 H43C 109.5 . .
H43A C43 H43C 109.5 . .
H43B C43 H43C 109.5 . .
C13 C20 H20A 109.5 . .
C13 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C13 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C54 1.754(3) .
C54 Cl1 1.754(3) 2
C54 H54A 0.9700 .
C54 H54B 0.9700 .
I1 C29 2.1474(19) .
O3 C30 1.227(2) .
O2 C24 1.241(2) .
N3 C30 1.366(2) .
N3 C25 1.477(2) .
N3 C28 1.488(2) .
C37 C42 1.383(3) .
C37 C38 1.395(3) .
C37 C28 1.507(3) .
O1 C22 1.242(2) .
C30 C31 1.506(3) .
C44 C45 1.383(3) .
C44 C49 1.388(3) .
C44 C27 1.516(3) .
O5 C47 1.373(2) .
O5 C50 1.419(3) .
N1 C9 1.346(3) .
N1 C7 1.386(3) .
N1 C6 1.448(3) .
C38 C39 1.388(3) .
C38 H38 0.9300 .
O4 C40 1.375(3) .
O4 C43 1.425(3) .
C29 C26 1.522(3) .
C29 C28 1.528(3) .
C29 H29 0.9800 .
C24 C23 1.421(3) .
C24 C25 1.551(3) .
C27 C23 1.512(3) .
C27 C26 1.550(3) .
C27 H27 0.9800 .
C31 C32 1.388(3) .
C31 C36 1.398(3) .
N2 C9 1.338(3) .
N2 C8 1.385(3) .
N2 C10 1.454(3) .
C23 C22 1.400(3) .
C34 C33 1.379(3) .
C34 C35 1.382(3) .
C34 H34 0.9300 .
C46 C47 1.380(3) .
C46 C45 1.389(3) .
C46 H46 0.9300 .
C22 C9 1.524(3) .
C32 C33 1.391(3) .
C32 H32 0.9300 .
C26 C25 1.534(3) .
C26 H26 0.9800 .
C35 C36 1.386(3) .
C35 H35 0.9300 .
C36 H36 0.9300 .
C41 C40 1.380(3) .
C41 C42 1.392(3) .
C41 H41 0.9300 .
C48 C47 1.382(3) .
C48 C49 1.386(3) .
C48 H48 0.9300 .
C45 H45 0.9300 .
C33 H33 0.9300 .
C39 C40 1.392(3) .
C39 H39 0.9300 .
C49 H49 0.9300 .
C28 H28 0.9800 .
C15 C14 1.390(3) .
C15 C10 1.392(3) .
C15 C21 1.502(3) .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C12 C13 1.385(4) .
C12 C11 1.389(4) .
C12 H12 0.9300 .
C42 H42 0.9300 .
C17 C3 1.512(4) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C6 C1 1.391(4) .
C6 C5 1.402(3) .
C18 C5 1.502(4) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C10 C11 1.400(3) .
C8 C7 1.335(4) .
C8 H8 0.9300 .
C14 C13 1.392(4) .
C14 H14 0.9300 .
C11 C19 1.505(4) .
C1 C2 1.393(3) .
C1 C16 1.510(3) .
C5 C4 1.390(4) .
C50 H50A 0.9600 .
C50 H50B 0.9600 .
C50 H50C 0.9600 .
C13 C20 1.514(4) .
C2 C3 1.390(4) .
C2 H2 0.9300 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C3 C4 1.374(4) .
C7 H7 0.9300 .
C4 H4 0.9300 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C25 H25 0.9800 .
C43 H43A 0.9600 .
C43 H43B 0.9600 .
C43 H43C 0.9600 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.194 0.250 243.1 45.3
2 0.155 0.093 0.414 7.4 -0.3
3 0.500 0.306 0.750 242.1 45.5
4 0.845 0.093 0.086 6.4 -0.2
5 0.345 0.406 0.586 6.7 -0.3
6 0.655 0.406 0.914 7.7 -0.2
7 0.500 0.694 0.250 243.1 45.3
8 0.000 0.806 0.750 242.1 45.5
9 0.345 0.593 0.086 6.4 -0.2
10 0.655 0.593 0.414 7.4 -0.3
11 0.155 0.906 0.914 7.7 -0.2
12 0.845 0.906 0.586 6.7 -0.3
