#------------------------------------------------------------------------------
#$Date: 2018-12-22 01:26:20 +0200 (Sat, 22 Dec 2018) $
#$Revision: 212740 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/03/1550382.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_1550382
loop_
_publ_author_name
'Peñuelas-Haro, Guillem'
'Ballester, Pablo'
_publ_section_title
;
 Efficient Hydrogen Bonding Recognition in Water using Aryl-extended
 Calix[4]pyrrole Receptors
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC05034A
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C74 H87 Cl4 N7 O6 P2'
_chemical_formula_weight         1374.24
_space_group_IT_number           109
_space_group_name_Hall           'I 4bw -2'
_space_group_name_H-M_alt        'I 41 m d'
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'I 4bw -2'
_symmetry_space_group_name_H-M   'I 41 m d'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-11-09 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.6411(4)
_cell_length_b                   19.6411(4)
_cell_length_c                   18.4185(5)
_cell_measurement_reflns_used    11169
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.2400
_cell_measurement_theta_min      2.0780
_cell_volume                     7105.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_molecular_graphics    'SHELXL-2018 (Sheldrick, 2018)'
_computing_publication_material  'SHELXL-2018 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2018)'
_computing_structure_solution    Sir2014
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25616
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.658
_diffrn_reflns_theta_min         2.074
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_current           24
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             2904
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1603 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4415
_refine_ls_number_restraints     188
_refine_ls_restrained_S_all      1.200
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1526
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.873
_reflns_number_gt                3877
_reflns_number_total             4415
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8sc05034a2.cif
_cod_data_source_block           gg-8_oo
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               1550382
_shelx_shelxl_version_number     2018/3
_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_min   0.980
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-y, x+1/2, z+1/4'
'y+1/2, -x, z+3/4'
'x, -y, z'
'-x+1/2, y+1/2, z+1/2'
'-y, -x+1/2, z+1/4'
'y+1/2, x, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1, z+1'
'-y+1/2, x+1, z+3/4'
'y+1, -x+1/2, z+5/4'
'x+1/2, -y+1/2, z+1/2'
'-x+1, y+1, z+1'
'-y+1/2, -x+1, z+3/4'
'y+1, x+1/2, z+5/4'
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
P1 P 1.000000 0.81777(6) 0.5890(2) 0.0270(3) Uani 1 2 d S T P . .
O1 O 0.93638(19) 0.77586(18) 0.6163(3) 0.0522(9) Uani 1 1 d . . . . .
N1 N 1.000000 0.6209(2) 0.4126(3) 0.0250(8) Uani 1 2 d S T P . .
H1 H 1.000001 0.598259 0.453804 0.030 Uiso 1 2 calc R U P . .
C1 C 0.84800(17) 0.55787(18) 0.3902(3) 0.0260(7) Uani 1 1 d . . . . .
O2 O 1.000000 0.8339(2) 0.5115(3) 0.0375(9) Uani 1 2 d S T P . .
N2 N 0.88146(19) 0.500000 0.4132(3) 0.0231(8) Uani 1 2 d S T P . .
H2N H 0.919114 0.500001 0.439082 0.028 Uiso 1 2 calc R U P . .
C2 C 0.7942(2) 0.5358(2) 0.3484(4) 0.0519(12) Uani 1 1 d . . . . .
H2 H 0.762504 0.564064 0.323818 0.062 Uiso 1 1 calc R U . . .
C3 C 0.87183(17) 0.62909(17) 0.4081(3) 0.0243(6) Uani 1 1 d . . . . .
C4 C 0.87616(16) 0.64206(17) 0.4910(3) 0.0231(7) Uani 1 1 d . . . . .
C5 C 0.85026(18) 0.59692(18) 0.5415(3) 0.0268(7) Uani 1 1 d . . . . .
H5 H 0.828231 0.556560 0.525526 0.032 Uiso 1 1 calc R U . . .
C6 C 0.85609(19) 0.60991(19) 0.6160(3) 0.0296(7) Uani 1 1 d . . . . .
H6 H 0.838937 0.577569 0.649704 0.036 Uiso 1 1 calc R U . . .
C7 C 0.88623(18) 0.66872(19) 0.6414(3) 0.0287(7) Uani 1 1 d . . . . .
C8 C 0.91036(18) 0.71425(19) 0.5896(3) 0.0307(7) Uani 1 1 d . . . . .
C9 C 0.90572(18) 0.7019(2) 0.5157(3) 0.0303(7) Uani 1 1 d . . . . .
H9 H 0.922754 0.734327 0.482019 0.036 Uiso 1 1 calc R U . . .
C10 C 0.82191(19) 0.6816(2) 0.3740(3) 0.0307(8) Uani 1 1 d . . . . .
H10A H 0.843872 0.726932 0.374430 0.037 Uiso 1 1 calc R U . . .
H10B H 0.814017 0.668939 0.322635 0.037 Uiso 1 1 calc R U . . .
C11 C 0.75280(19) 0.68704(19) 0.4123(3) 0.0330(8) Uani 1 1 d D . . . .
H11A H 0.730647 0.641808 0.414361 0.040 Uiso 0.5 1 calc R U P A 1
H11B H 0.759075 0.703722 0.462592 0.040 Uiso 0.5 1 calc R U P A 1
H11C H 0.740200 0.641686 0.431526 0.040 Uiso 0.4 1 calc R U P B 2
H11D H 0.757304 0.718386 0.454132 0.040 Uiso 0.4 1 calc R U P B 2
H11E H 0.762328 0.691273 0.464901 0.040 Uiso 0.1 1 calc R U P C 3
H11F H 0.729484 0.642824 0.405426 0.040 Uiso 0.1 1 calc R U P C 3
C12 C 0.7085(3) 0.7368(5) 0.3693(6) 0.028(2) Uani 0.5 1 d D U P D 1
H12A H 0.700489 0.717956 0.320240 0.034 Uiso 0.5 1 calc R U P D 1
H12B H 0.733468 0.780282 0.363683 0.034 Uiso 0.5 1 calc R U P D 1
C13 C 0.6397(5) 0.7510(4) 0.4056(7) 0.038(2) Uani 0.5 1 d D U P D 1
H13A H 0.616022 0.788264 0.379776 0.045 Uiso 0.5 1 calc R U P D 1
H13B H 0.646889 0.765225 0.456610 0.045 Uiso 0.5 1 calc R U P D 1
Cl1 Cl 0.58893(14) 0.6751(2) 0.4030(3) 0.0885(11) Uani 0.5 1 d D U P D 1
C12' C 0.6954(5) 0.7126(7) 0.3631(6) 0.044(4) Uani 0.4 1 d D U P D 2
H12C H 0.686229 0.678218 0.325012 0.053 Uiso 0.4 1 calc R U P D 2
H12D H 0.710088 0.755089 0.338764 0.053 Uiso 0.4 1 calc R U P D 2
C13' C 0.6297(6) 0.7263(5) 0.4058(10) 0.038(5) Uani 0.4 1 d D U P D 2
H13C H 0.621586 0.688964 0.440876 0.045 Uiso 0.4 1 calc R U P D 2
H13D H 0.590460 0.728309 0.372101 0.045 Uiso 0.4 1 calc R U P D 2
Cl1' Cl 0.6379(2) 0.80563(19) 0.4532(4) 0.0807(13) Uani 0.4 1 d D U P D 2
C12" C 0.6985(10) 0.745(2) 0.392(2) 0.021(10) Uani 0.1 1 d D U P D 3
H12E H 0.703233 0.782770 0.428067 0.025 Uiso 0.1 1 calc R U P D 3
H12F H 0.710217 0.764053 0.344074 0.025 Uiso 0.1 1 calc R U P D 3
C13" C 0.6236(12) 0.7229(11) 0.391(4) 0.032(14) Uani 0.1 1 d D U P D 3
H13E H 0.614960 0.689858 0.430590 0.039 Uiso 0.1 1 calc R U P D 3
H13F H 0.613209 0.700353 0.344209 0.039 Uiso 0.1 1 calc R U P D 3
Cl1" Cl 0.5701(6) 0.7961(7) 0.4024(10) 0.066(4) Uani 0.1 1 d D U P D 3
C15 C 1.000000 0.8881(3) 0.6494(4) 0.0421(13) Uani 1 2 d S T P . .
H15A H 1.040607 0.916240 0.638902 0.050 Uiso 0.5 1 calc R U P . .
H15B H 0.959393 0.916240 0.638902 0.050 Uiso 0.5 1 calc R U P . .
C16 C 1.000000 0.8716(4) 0.7288(4) 0.071(2) Uani 1 2 d S T P . .
H16A H 0.953591 0.860532 0.744312 0.106 Uiso 0.5 1 calc R U P . .
H16B H 1.016544 0.911042 0.756211 0.106 Uiso 0.5 1 calc R U P . .
H16C H 1.029865 0.832552 0.737721 0.106 Uiso 0.5 1 calc R U P . .
C17 C 0.8921(3) 0.6830(3) 0.7213(3) 0.0438(10) Uani 1 1 d . . . . .
H17A H 0.870960 0.727046 0.732248 0.066 Uiso 1 1 calc R U . . .
H17B H 0.940295 0.684337 0.735136 0.066 Uiso 1 1 calc R U . . .
H17C H 0.868967 0.647070 0.748719 0.066 Uiso 1 1 calc R U . . .
C18 C 0.94249(17) 0.64100(18) 0.3760(3) 0.0252(7) Uani 1 1 d . . . . .
C19 C 0.96391(19) 0.67207(18) 0.3131(3) 0.0285(7) Uani 1 1 d . . . . .
H19 H 0.935412 0.690268 0.276210 0.034 Uiso 1 1 calc R U . . .
N1A N 1.000000 0.500000 0.5348(4) 0.0287(13) Uani 1 4 d DS T P . .
C1A C 1.000000 0.500000 0.5971(4) 0.0285(14) Uani 1 4 d DS T P . .
C2A C 1.000000 0.500000 0.6761(5) 0.046(2) Uani 1 4 d DS T P . .
H2AA H 0.982646 0.456276 0.693854 0.070 Uiso 0.25 1 calc R U P . .
H2AB H 0.970811 0.536891 0.693854 0.070 Uiso 0.25 1 calc R U P . .
H2AC H 1.046543 0.506833 0.693854 0.070 Uiso 0.25 1 calc R U P . .
N1B N 0.9595(16) 0.4317(11) 0.1357(10) 0.094(7) Uani 0.25 1 d D U P E -1
C1B C 0.9704(12) 0.4574(11) 0.1905(9) 0.070(5) Uani 0.25 1 d D U P E -1
C2B C 0.9904(18) 0.493(2) 0.2565(7) 0.063(6) Uani 0.25 1 d D U P E -1
H2B1 H 0.962387 0.532450 0.263166 0.094 Uiso 0.25 1 d R U P E -1
H2B2 H 1.037279 0.506364 0.253572 0.094 Uiso 0.25 1 d R U P E -1
H2B3 H 0.984354 0.462524 0.296859 0.094 Uiso 0.25 1 d R U P E -1
N1C N 1.000000 0.3812(10) 0.0953(9) 0.057(4) Uani 0.3 2 d DS TU P F 2
C1C C 1.000000 0.3730(18) 0.0336(10) 0.080(7) Uani 0.3 2 d DS TU P F 2
C2C C 1.000000 0.364(2) -0.0448(9) 0.100(9) Uani 0.3 2 d DS TU P F 2
H2C1 H 0.971658 0.397840 -0.067396 0.150 Uiso 0.15 1 d R U P F 2
H2C2 H 0.982703 0.319558 -0.055684 0.150 Uiso 0.15 1 d R U P F 2
H2C3 H 1.045638 0.368171 -0.062957 0.150 Uiso 0.15 1 d R U P F 2
N1C' N 1.000000 0.3756(14) -0.1438(9) 0.051(6) Uani 0.2 2 d DS TU P G 1
C1C' C 1.000000 0.3627(13) -0.0830(9) 0.044(6) Uani 0.2 2 d DS TU P G 1
C2C' C 1.000000 0.361(2) -0.0039(9) 0.061(8) Uani 0.2 2 d DS TU P G 1
H2C4 H 1.045887 0.356535 0.013355 0.092 Uiso 0.1 1 d R U P G 1
H2C5 H 0.973394 0.323150 0.012421 0.092 Uiso 0.1 1 d R U P G 1
H2C6 H 0.980719 0.402601 0.014643 0.092 Uiso 0.1 1 d R U P G 1
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'
P P 0.1023 0.0942 '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
O2 P1 O1 115.13(15) . 14_644
O2 P1 O1 115.13(15) . .
O1 P1 O1 104.6(3) 14_644 .
O2 P1 C15 116.3(3) . .
O1 P1 C15 101.86(18) 14_644 .
O1 P1 C15 101.86(17) . .
C8 O1 P1 128.8(3) . .
C18 N1 C18 110.7(4) 14_644 .
C18 N1 H1 124.6 14_644 .
C18 N1 H1 124.6 . .
C2 C1 N2 106.1(3) . .
C2 C1 C3 130.6(3) . .
N2 C1 C3 123.2(3) . .
C1 N2 C1 111.0(4) . 5_565
C1 N2 H2N 124.5 . .
C1 N2 H2N 124.5 5_565 .
C1 C2 C2 108.4(2) . 5_565
C1 C2 H2 125.8 . .
C2 C2 H2 125.8 5_565 .
C1 C3 C18 109.8(3) . .
C1 C3 C4 112.6(3) . .
C18 C3 C4 107.8(3) . .
C1 C3 C10 109.3(3) . .
C18 C3 C10 108.4(3) . .
C4 C3 C10 108.9(3) . .
C5 C4 C9 118.4(3) . .
C5 C4 C3 122.5(3) . .
C9 C4 C3 119.0(3) . .
C4 C5 C6 120.9(3) . .
C4 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
C7 C6 C5 121.4(3) . .
C7 C6 H6 119.3 . .
C5 C6 H6 119.3 . .
C6 C7 C8 116.8(3) . .
C6 C7 C17 121.5(3) . .
C8 C7 C17 121.7(4) . .
C9 C8 C7 122.6(3) . .
C9 C8 O1 121.3(3) . .
C7 C8 O1 116.0(3) . .
C8 C9 C4 119.9(3) . .
C8 C9 H9 120.1 . .
C4 C9 H9 120.1 . .
C11 C10 C3 114.7(3) . .
C11 C10 H10A 108.6 . .
C3 C10 H10A 108.6 . .
C11 C10 H10B 108.6 . .
C3 C10 H10B 108.6 . .
H10A C10 H10B 107.6 . .
C12 C11 C10 108.0(4) . .
C12' C11 C10 113.7(5) . .
C10 C11 C12" 122.2(13) . .
C12 C11 H11A 110.1 . .
C10 C11 H11A 110.1 . .
C12 C11 H11B 110.1 . .
C10 C11 H11B 110.1 . .
H11A C11 H11B 108.4 . .
C12' C11 H11C 108.8 . .
C10 C11 H11C 108.8 . .
C12' C11 H11D 108.8 . .
C10 C11 H11D 108.8 . .
H11C C11 H11D 107.7 . .
C10 C11 H11E 106.8 . .
C12" C11 H11E 106.8 . .
C10 C11 H11F 106.8 . .
C12" C11 H11F 106.8 . .
H11E C11 H11F 106.6 . .
C11 C12 C13 113.1(7) . .
C11 C12 H12A 109.0 . .
C13 C12 H12A 109.0 . .
C11 C12 H12B 109.0 . .
C13 C12 H12B 109.0 . .
H12A C12 H12B 107.8 . .
C12 C13 Cl1 109.1(6) . .
C12 C13 H13A 109.9 . .
Cl1 C13 H13A 109.9 . .
C12 C13 H13B 109.9 . .
Cl1 C13 H13B 109.9 . .
H13A C13 H13B 108.3 . .
C11 C12' C13' 111.9(9) . .
C11 C12' H12C 109.2 . .
C13' C12' H12C 109.2 . .
C11 C12' H12D 109.2 . .
C13' C12' H12D 109.2 . .
H12C C12' H12D 107.9 . .
C12' C13' Cl1' 109.0(7) . .
C12' C13' H13C 109.9 . .
Cl1' C13' H13C 109.9 . .
C12' C13' H13D 109.9 . .
Cl1' C13' H13D 109.9 . .
H13C C13' H13D 108.3 . .
C13" C12" C11 116(3) . .
C13" C12" H12E 108.3 . .
C11 C12" H12E 108.3 . .
C13" C12" H12F 108.3 . .
C11 C12" H12F 108.3 . .
H12E C12" H12F 107.4 . .
C12" C13" Cl1" 109.2(9) . .
C12" C13" H13E 109.8 . .
Cl1" C13" H13E 109.8 . .
C12" C13" H13F 109.8 . .
Cl1" C13" H13F 109.8 . .
H13E C13" H13F 108.3 . .
C16 C15 P1 116.4(5) . .
C16 C15 H15A 108.2 . .
P1 C15 H15A 108.2 . .
C16 C15 H15B 108.2 . .
P1 C15 H15B 108.2 . .
H15A C15 H15B 107.3 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C15 C16 H16A 109.5(5) . 14_644
H16A C16 H16A 136.9 . 14_644
H16B C16 H16A 73.5 . 14_644
H16C C16 H16A 38.7 . 14_644
C15 C16 H16B 109.5(12) . 14_644
H16A C16 H16B 73.5 . 14_644
H16B C16 H16B 38.7 . 14_644
H16C C16 H16B 136.9 . 14_644
H16A C16 H16B 109.5 14_644 14_644
C15 C16 H16C 109.5(18) . 14_644
H16A C16 H16C 38.7 . 14_644
H16B C16 H16C 136.9 . 14_644
H16C C16 H16C 73.5 . 14_644
H16A C16 H16C 109.5 14_644 14_644
H16B C16 H16C 109.5 14_644 14_644
C7 C17 H17A 109.5 . .
C7 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C7 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
N1 C18 C19 106.8(3) . .
N1 C18 C3 121.0(3) . .
C19 C18 C3 132.2(3) . .
C18 C19 C19 107.8(2) . 14_644
C18 C19 H19 126.1 . .
C19 C19 H19 126.1 14_644 .
N1A C1A C2A 180.0 . .
C1A C2A H2AA 109.5 . .
C1A C2A H2AB 109.5 . .
H2AA C2A H2AB 109.5 . .
C1A C2A H2AC 109.5 . .
H2AA C2A H2AC 109.5 . .
H2AB C2A H2AC 109.5 . .
C1A C2A H2AA 109.47(6) . 10_654
H2AA C2A H2AA 141.1 . 10_654
H2AB C2A H2AA 56.2 . 10_654
H2AC C2A H2AA 56.3 . 10_654
C1A C2A H2AA 109(5) . 5_565
H2AA C2A H2AA 122.4 . 5_565
H2AB C2A H2AA 15.7 . 5_565
H2AC C2A H2AA 95.4 . 5_565
H2AA C2A H2AA 40.7 10_654 5_565
C1A C2A H2AA 109(5) . 14_644
H2AA C2A H2AA 40.7 . 14_644
H2AB C2A H2AA 137.8 . 14_644
H2AC C2A H2AA 71.6 . 14_644
H2AA C2A H2AA 122.4 10_654 14_644
H2AA C2A H2AA 141.1 5_565 14_644
C1A C2A H2AB 109.471(3) . 10_654
H2AA C2A H2AB 56.3 . 10_654
H2AB C2A H2AB 141.1 . 10_654
H2AC C2A H2AB 56.3 . 10_654
H2AA C2A H2AB 109.5 10_654 10_654
H2AA C2A H2AB 137.8 5_565 10_654
H2AA C2A H2AB 15.7 14_644 10_654
C1A C2A H2AB 109(7) . 5_565
H2AA C2A H2AB 15.7 . 5_565
H2AB C2A H2AB 95.4 . 5_565
H2AC C2A H2AB 122.4 . 5_565
H2AA C2A H2AB 137.8 10_654 5_565
H2AA C2A H2AB 109.5 5_565 5_565
H2AA C2A H2AB 56.2 14_644 5_565
H2AB C2A H2AB 71.6 10_654 5_565
C1A C2A H2AB 109(7) . 14_644
H2AA C2A H2AB 137.8 . 14_644
H2AB C2A H2AB 71.6 . 14_644
H2AC C2A H2AB 40.7 . 14_644
H2AA C2A H2AB 15.7 10_654 14_644
H2AA C2A H2AB 56.2 5_565 14_644
H2AA C2A H2AB 109.5 14_644 14_644
H2AB C2A H2AB 95.4 10_654 14_644
H2AB C2A H2AB 141.1 5_565 14_644
C1A C2A H2AC 109.47(5) . 10_654
H2AA C2A H2AC 56.2 . 10_654
H2AB C2A H2AC 56.3 . 10_654
H2AC C2A H2AC 141.1 . 10_654
H2AA C2A H2AC 109.5 10_654 10_654
H2AA C2A H2AC 71.6 5_565 10_654
H2AA C2A H2AC 95.4 14_644 10_654
H2AB C2A H2AC 109.5 10_654 10_654
H2AB C2A H2AC 40.7 5_565 10_654
H2AB C2A H2AC 122.4 14_644 10_654
C1A C2A H2AC 109(2) . 5_565
H2AA C2A H2AC 95.4 . 5_565
H2AB C2A H2AC 122.4 . 5_565
H2AC C2A H2AC 15.7 . 5_565
H2AA C2A H2AC 71.6 10_654 5_565
H2AA C2A H2AC 109.5 5_565 5_565
H2AA C2A H2AC 56.3 14_644 5_565
H2AB C2A H2AC 40.7 10_654 5_565
H2AB C2A H2AC 109.5 5_565 5_565
H2AB C2A H2AC 56.3 14_644 5_565
H2AC C2A H2AC 137.8 10_654 5_565
C1A C2A H2AC 109(2) . 14_644
H2AA C2A H2AC 71.6 . 14_644
H2AB C2A H2AC 40.7 . 14_644
H2AC C2A H2AC 137.8 . 14_644
H2AA C2A H2AC 95.4 10_654 14_644
H2AA C2A H2AC 56.3 5_565 14_644
H2AA C2A H2AC 109.5 14_644 14_644
H2AB C2A H2AC 122.4 10_654 14_644
H2AB C2A H2AC 56.3 5_565 14_644
H2AB C2A H2AC 109.5 14_644 14_644
H2AC C2A H2AC 15.7 10_654 14_644
H2AC C2A H2AC 141.1 5_565 14_644
N1B C1B C2B 174(3) . .
C1B C2B H2B1 109.9 . .
C1B C2B H2B2 110.1 . .
H2B1 C2B H2B2 109.5 . .
C1B C2B H2B3 108.5 . .
H2B1 C2B H2B3 109.5 . .
H2B2 C2B H2B3 109.5 . .
N1C C1C C2C 179(4) . .
H2C4 C1C H2C5 90.4 14_644 14_644
N1C C1C H2C6 110(3) . 14_644
C2C C1C H2C6 69(3) . 14_644
H2C4 C1C H2C6 120.0 14_644 14_644
H2C5 C1C H2C6 104.9 14_644 14_644
C1C C2C H2C1 110.3 . .
C1C C2C H2C2 108.5 . .
H2C1 C2C H2C2 109.5 . .
C1C C2C H2C3 109.6 . .
H2C1 C2C H2C3 109.5 . .
H2C2 C2C H2C3 109.5 . .
H2C4 C2C H2C5 67.2 14_644 14_644
C1C C2C H2C6 31.6(18) . 14_644
H2C1 C2C H2C6 97.2 . 14_644
H2C2 C2C H2C6 139.5 . 14_644
H2C3 C2C H2C6 88.6 . 14_644
H2C1 C2C H2C6 78.9 14_644 14_644
H2C2 C2C H2C6 124.5 14_644 14_644
H2C3 C2C H2C6 119.1 14_644 14_644
H2C4 C2C H2C6 68.3 14_644 14_644
H2C5 C2C H2C6 67.8 14_644 14_644
N1C' C1C' C2C' 168(2) . .
N1C' C1C' H2C1 98(2) . 14_644
C2C' C1C' H2C1 73(2) . 14_644
N1C' C1C' H2C2 131(2) . 14_644
C2C' C1C' H2C2 60(2) . 14_644
N1C' C1C' H2C3 110.2(16) . 14_644
C2C' C1C' H2C3 67.9(13) . 14_644
C1C' C2C' H2C4 109.4 . .
C1C' C2C' H2C5 109.2 . .
H2C4 C2C' H2C5 109.5 . .
C1C' C2C' H2C6 109.8 . .
H2C4 C2C' H2C6 109.5 . .
H2C5 C2C' H2C6 109.5 . .
C1C' C2C' H2C1 37.0(14) . 14_644
H2C4 C2C' H2C1 87.4 . 14_644
H2C5 C2C' H2C1 146.1 . 14_644
H2C6 C2C' H2C1 91.0 . 14_644
C1C' C2C' H2C2 44.0(19) . 14_644
H2C4 C2C' H2C2 86.4 . 14_644
H2C5 C2C' H2C2 83.3 . 14_644
H2C6 C2C' H2C2 153.6 . 14_644
C1C' C2C' H2C3 39.7(7) . 14_644
H2C4 C2C' H2C3 149.1 . 14_644
H2C5 C2C' H2C3 88.4 . 14_644
H2C6 C2C' H2C3 86.6 . 14_644
C1C' C2C' H2C4 109.44(16) . 14_644
H2C4 C2C' H2C4 139.7 . 14_644
H2C5 C2C' H2C4 46.5 . 14_644
H2C6 C2C' H2C4 66.0 . 14_644
C1C' C2C' H2C5 109.2(13) . 14_644
H2C4 C2C' H2C5 46.5 . 14_644
H2C5 C2C' H2C5 66.0 . 14_644
H2C6 C2C' H2C5 139.7 . 14_644
H2C4 C2C' H2C5 109.5 14_644 14_644
C1C' C2C' H2C6 109.8(14) . 14_644
H2C4 C2C' H2C6 66.0 . 14_644
H2C5 C2C' H2C6 139.7 . 14_644
H2C6 C2C' H2C6 46.5 . 14_644
H2C1 C2C' H2C6 73.8 14_644 14_644
H2C2 C2C' H2C6 133.6 14_644 14_644
H2C3 C2C' H2C6 116.2 14_644 14_644
H2C4 C2C' H2C6 109.5 14_644 14_644
H2C5 C2C' H2C6 109.5 14_644 14_644
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O2 1.462(4) .
P1 O1 1.579(3) 14_644
P1 O1 1.579(3) .
P1 C15 1.774(6) .
O1 C8 1.403(5) .
N1 C18 1.373(4) 14_644
N1 C18 1.373(4) .
N1 H1 0.8800 .
C1 C2 1.377(5) .
C1 N2 1.380(4) .
C1 C3 1.511(5) .
N2 H2N 0.8800 .
C2 C2 1.405(9) 5_565
C2 H2 0.9500 .
C3 C18 1.526(5) .
C3 C4 1.550(4) .
C3 C10 1.555(4) .
C4 C5 1.383(5) .
C4 C9 1.388(5) .
C5 C6 1.399(5) .
C5 H5 0.9500 .
C6 C7 1.380(6) .
C6 H6 0.9500 .
C7 C8 1.391(5) .
C7 C17 1.503(5) .
C8 C9 1.386(5) .
C9 H9 0.9500 .
C10 C11 1.534(5) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.529(6) .
C11 C12' 1.532(7) .
C11 C12" 1.61(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C11 H11C 0.9900 .
C11 H11D 0.9900 .
C11 H11E 0.9900 .
C11 H11F 0.9900 .
C12 C13 1.533(5) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 Cl1 1.793(8) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C12' C13' 1.535(5) .
C12' H12C 0.9900 .
C12' H12D 0.9900 .
C13' Cl1' 1.794(8) .
C13' H13C 0.9900 .
C13' H13D 0.9900 .
C12" C13" 1.537(5) .
C12" H12E 0.9900 .
C12" H12F 0.9900 .
C13" Cl1" 1.793(9) .
C13" H13E 0.9900 .
C13" H13F 0.9900 .
C15 C16 1.496(9) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C16 H16A 0.98(3) 14_644
C16 H16B 0.98(5) 14_644
C16 H16C 0.98(8) 14_644
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 C19 1.376(5) .
C19 C19 1.418(7) 14_644
C19 H19 0.9500 .
N1A C1A 1.147(8) .
C1A C2A 1.455(9) .
C2A H2AA 0.9800 .
C2A H2AB 0.9800 .
C2A H2AC 0.9800 .
C2A H2AA 0.9800 10_654
C2A H2AA 0.9600 5_565
C2A H2AA 0.9600 14_644
C2A H2AB 0.9800 10_654
C2A H2AB 0.9600 5_565
C2A H2AB 0.9600 14_644
C2A H2AC 0.9800 10_654
C2A H2AC 0.98(10) 5_565
C2A H2AC 0.98(10) 14_644
N1B C1B 1.147(8) .
C1B C2B 1.456(10) .
C2B H2B1 0.9600 .
C2B H2B2 0.9600 .
C2B H2B3 0.9600 .
N1C C1C 1.147(8) .
C1C C2C 1.455(9) .
C2C H2C1 0.9600 .
C2C H2C2 0.9600 .
C2C H2C3 0.9600 .
C2C H2C1 0.9600 14_644
C2C H2C2 0.9600 14_644
C2C H2C3 0.9600 14_644
N1C' C1C' 1.149(9) .
C1C' C2C' 1.457(9) .
C2C' H2C4 0.9600 .
C2C' H2C5 0.9600 .
C2C' H2C6 0.9600 .
C2C' H2C4 0.9599 14_644
C2C' H2C5 0.9600 14_644
C2C' H2C6 0.9600 14_644
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_4
O2 P1 O1 C8 53.4(5) . .
O1 P1 O1 C8 -74.0(5) 14_644 .
C15 P1 O1 C8 -179.8(4) . .
C2 C1 N2 C1 -3.2(5) . 5_565
C3 C1 N2 C1 178.9(2) . 5_565
N2 C1 C2 C2 1.9(3) . 5_565
C3 C1 C2 C2 179.5(3) . 5_565
C2 C1 C3 C18 -115.7(5) . .
N2 C1 C3 C18 61.6(4) . .
C2 C1 C3 C4 124.2(5) . .
N2 C1 C3 C4 -58.5(4) . .
C2 C1 C3 C10 3.1(6) . .
N2 C1 C3 C10 -179.6(3) . .
C1 C3 C4 C5 -9.9(4) . .
C18 C3 C4 C5 -131.2(3) . .
C10 C3 C4 C5 111.4(4) . .
C1 C3 C4 C9 171.6(3) . .
C18 C3 C4 C9 50.3(4) . .
C10 C3 C4 C9 -67.1(4) . .
C9 C4 C5 C6 -2.5(5) . .
C3 C4 C5 C6 179.0(3) . .
C4 C5 C6 C7 1.6(5) . .
C5 C6 C7 C8 0.1(5) . .
C5 C6 C7 C17 179.6(3) . .
C6 C7 C8 C9 -0.8(5) . .
C17 C7 C8 C9 179.7(4) . .
C6 C7 C8 O1 175.6(3) . .
C17 C7 C8 O1 -3.9(5) . .
P1 O1 C8 C9 -42.0(6) . .
P1 O1 C8 C7 141.6(4) . .
C7 C8 C9 C4 -0.1(6) . .
O1 C8 C9 C4 -176.3(4) . .
C5 C4 C9 C8 1.7(5) . .
C3 C4 C9 C8 -179.7(3) . .
C1 C3 C10 C11 73.2(4) . .
C18 C3 C10 C11 -167.1(3) . .
C4 C3 C10 C11 -50.1(4) . .
C3 C10 C11 C12 -176.3(6) . .
C3 C10 C11 C12' -154.8(7) . .
C3 C10 C11 C12" 171.3(17) . .
C10 C11 C12 C13 -175.5(7) . .
C11 C12 C13 Cl1 -67.8(11) . .
C10 C11 C12' C13' -172.5(7) . .
C11 C12' C13' Cl1' 77.4(13) . .
C10 C11 C12" C13" 141(3) . .
C11 C12" C13" Cl1" 158(3) . .
O2 P1 C15 C16 180.000(3) . .
O1 P1 C15 C16 -53.97(17) 14_644 .
O1 P1 C15 C16 53.97(17) . .
C18 N1 C18 C19 2.6(5) 14_644 .
C18 N1 C18 C3 -175.8(2) 14_644 .
C1 C3 C18 N1 -84.4(4) . .
C4 C3 C18 N1 38.6(4) . .
C10 C3 C18 N1 156.3(4) . .
C1 C3 C18 C19 97.7(4) . .
C4 C3 C18 C19 -139.3(4) . .
C10 C3 C18 C19 -21.6(5) . .
N1 C18 C19 C19 -1.6(3) . 14_644
C3 C18 C19 C19 176.6(3) . 14_644
