#------------------------------------------------------------------------------
#$Date: 2016-02-13 21:28:24 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176429 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/79/7117966.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_7117966
loop_
_publ_author_name
'Guobao Huang'
'Zhenfeng He'
'Chen-Xi Cai'
'Fangfang Pan'
'Dingqiao Yang'
'Kari Rissanen'
'Wei Jiang'
_publ_section_title
;
 Bis-urea macrocycles with a deep cavity
;
_journal_name_full               Chem.Commun.
_journal_page_first              15490
_journal_paper_doi               10.1039/C5cc06768E
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety
'C68 H70 N4 O10, 7.7(C2 H3 N), 0.3(C H2 Cl2), 2(H2 O)'
_chemical_formula_sum            'C83.7 H97.7 Cl0.6 N11.7 O12'
_chemical_formula_weight         1480.90
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   other
_audit_creation_date             2015-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-08-09 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                105.227(3)
_cell_angle_beta                 99.554(3)
_cell_angle_gamma                102.607(2)
_cell_formula_units_Z            1
_cell_length_a                   11.6914(4)
_cell_length_b                   13.3995(3)
_cell_length_c                   13.6649(5)
_cell_measurement_reflns_used    7738
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      76.5160
_cell_measurement_theta_min      3.5400
_cell_volume                     1958.27(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
  1 omega  -48.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000   60.0000 81

  2 omega  -32.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000 -150.0000 61

  3 omega   34.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013 -125.0000  -60.0000 62

  4 omega   40.00  103.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   30.0000 63

  5 omega   77.00  104.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   60.0000 27

  6 omega   50.00  123.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -130.0000   16.0000 73

  7 omega   55.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 36

  8 omega   47.00   74.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 27

  9 omega   41.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 46

 10 omega   60.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -120.0000 35

 11 omega   91.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 25

 12 omega   54.00   84.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 30

 13 omega   47.00   84.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 37

 14 omega   37.00  144.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   90.0000 107

 15 omega   42.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  150.0000 49

 16 omega   32.00  160.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000    0.0000 128

 17 omega   94.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -180.0000 84

 18 omega   40.00   66.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 26

 19 omega   38.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 31

 20 omega  -95.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  125.0000   60.0000 74

 21 omega -117.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -19.0000 -120.0000 107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0865811000
_diffrn_orient_matrix_UB_12      -0.0054729000
_diffrn_orient_matrix_UB_13      -0.0736053000
_diffrn_orient_matrix_UB_21      -0.1084485000
_diffrn_orient_matrix_UB_22      -0.0396769000
_diffrn_orient_matrix_UB_23      -0.0950386000
_diffrn_orient_matrix_UB_31      0.0077718000
_diffrn_orient_matrix_UB_32      0.1172906000
_diffrn_orient_matrix_UB_33      0.0038852000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14442
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         76.936
_diffrn_reflns_theta_min         3.450
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.868
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_correction_T_min  0.698
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             788
_exptl_crystal_size_max          0.3628
_exptl_crystal_size_mid          0.3119
_exptl_crystal_size_min          0.1031
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         8014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0679
_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)+(0.1314P)²+0.6904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1987
_refine_ls_wR_factor_ref         0.2084
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6943
_reflns_number_total             8014
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc06768e2.cif
_cod_data_source_block           ACN@1-anti
_cod_original_cell_volume        1958.27(11)
_cod_original_formula_sum        'C83.70 H97.70 Cl0.60 N11.70 O12'
_cod_database_code               7117966
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_formula         'C80 H100 O20 Cl2'
_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 99.96
_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, All C(H,H,H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C39) = Uanis(C40)
3. Others
 Fixed Sof: H12(0.5) H12A(0.5) C13(0.5) H13A(0.5) H13B(0.5) C13B(0.5)
 H13C(0.5) H13D(0.5) H14A(0.5) H14B(0.5) H14C(0.5) H14D(0.5) H14E(0.5)
 H14F(0.5) C40(0.85) H40A(0.85) H40B(0.85) H40C(0.85) C41(0.85) N3(0.85)
 C39(0.15) H39A(0.15) H39B(0.15) Cl1(0.15) Cl3(0.15)
4.a Ternary CH refined with riding coordinates:
 C15(H15), C17(H17)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C13B(H13C,H13D), C16(H16A,H16B), C28(H28A,
 H28B), C29(H29A,H29B), C30(H30A,H30B), C32(H32A,H32B), C34(H34A,H34B),
 C39(H39A,H39B)
4.c Me refined with riding coordinates:
 C14(H14A,H14B,H14C), C14(H14D,H14E,H14F)
4.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C12(H12), C12(H12A), C21(H21), C22(H22),
 C24(H24), C25(H25), N1(H1), N2(H2)
4.e Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C38(H38A,H38B,H38C), C36(H36A,H36B,H36C), C40(H40A,H40B,
 H40C), C9DA(H9DA,H9DB,H9DC)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_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
C1 C 0.53829(19) 0.62201(13) -0.06496(13) 0.0319(4) Uani 1 1 d . . . . .
C2 C 0.43599(18) 0.61275(13) -0.02073(13) 0.0301(4) Uani 1 1 d . . . . .
C3 C 0.45122(17) 0.63822(12) 0.09012(13) 0.0270(4) Uani 1 1 d . . . . .
C4 C 0.57041(18) 0.66847(13) 0.15091(13) 0.0311(4) Uani 1 1 d . . . . .
H4 H 0.5829 0.6833 0.2229 0.037 Uiso 1 1 calc R . . . .
C5 C 0.66837(19) 0.67674(14) 0.10787(15) 0.0349(4) Uani 1 1 d . . . . .
H5 H 0.7456 0.6960 0.1505 0.042 Uiso 1 1 calc R . . . .
C6 C 0.65273(19) 0.65621(13) -0.00093(15) 0.0338(4) Uani 1 1 d . . . . .
C7 C 0.3164(2) 0.57929(15) -0.08357(14) 0.0368(4) Uani 1 1 d . . . . .
H7 H 0.3043 0.5648 -0.1555 0.044 Uiso 1 1 calc R . . . .
C8 C 0.2193(2) 0.56811(16) -0.04065(15) 0.0401(4) Uani 1 1 d . . . . .
H8 H 0.1417 0.5438 -0.0834 0.048 Uiso 1 1 calc R . . . .
C9 C 0.23613(19) 0.59349(14) 0.06890(15) 0.0343(4) Uani 1 1 d . . . . .
C10 C 0.34875(17) 0.63188(12) 0.13522(13) 0.0284(4) Uani 1 1 d . . . . .
C11 C 0.8679(2) 0.6998(2) 0.0145(2) 0.0595(7) Uani 1 1 d . . . . .
H11A H 0.8805 0.6466 0.0485 0.071 Uiso 1 1 calc R . . . .
H11B H 0.8824 0.7682 0.0679 0.071 Uiso 1 1 calc R . . . .
C12 C 0.9526(3) 0.7099(2) -0.0572(3) 0.0797(11) Uani 1 1 d . . . . .
H12 H 0.9283 0.6689 -0.1273 0.096 Uiso 0.5 1 calc R . P A 1
H12A H 0.9816 0.6533 -0.0886 0.096 Uiso 0.5 1 calc R . P B 2
C13 C 1.0662(5) 0.7809(5) -0.0172(5) 0.0569(12) Uani 0.5 1 d . . P C 1
H13A H 1.1106 0.7712 -0.0714 0.068 Uiso 0.5 1 calc R . P C 1
H13B H 1.1070 0.7606 0.0392 0.068 Uiso 0.5 1 calc R . P C 1
C13B C 0.9833(5) 0.8077(4) -0.0726(4) 0.0550(12) Uani 0.5 1 d . . P C 2
H13C H 0.9104 0.8294 -0.0892 0.066 Uiso 0.5 1 calc R . P C 2
H13D H 1.0187 0.8004 -0.1326 0.066 Uiso 0.5 1 calc R . P C 2
C14 C 1.0753(4) 0.9004(3) 0.0240(3) 0.0832(10) Uani 1 1 d . . . . .
H14A H 1.1586 0.9407 0.0494 0.125 Uiso 0.5 1 calc R . P C 1
H14B H 1.0382 0.9232 -0.0313 0.125 Uiso 0.5 1 calc R . P C 1
H14C H 1.0347 0.9126 0.0798 0.125 Uiso 0.5 1 calc R . P C 1
H14D H 1.0922 0.9663 0.0069 0.125 Uiso 0.5 1 calc R . P C 2
H14E H 1.0404 0.9100 0.0835 0.125 Uiso 0.5 1 calc R . P C 2
H14F H 1.1488 0.8809 0.0400 0.125 Uiso 0.5 1 calc R . P C 2
C15 C 0.35886(17) 0.66851(13) 0.25307(13) 0.0288(4) Uani 1 1 d . . . . .
H15 H 0.4321 0.6585 0.2911 0.035 Uiso 1 1 calc R . . . .
C16 C 0.24580(19) 0.60294(14) 0.27393(15) 0.0356(4) Uani 1 1 d . . . . .
H16A H 0.2433 0.5273 0.2545 0.043 Uiso 1 1 calc R . . . .
H16B H 0.2464 0.6273 0.3475 0.043 Uiso 1 1 calc R . . . .
C17 C 0.13767(19) 0.61898(15) 0.20941(16) 0.0375(4) Uani 1 1 d . . . . .
H17 H 0.0651 0.5800 0.2249 0.045 Uiso 1 1 calc R . . . .
C18 C 0.55828(17) 1.07257(13) 0.39964(12) 0.0270(3) Uani 1 1 d . . . . .
C19 C 0.45350(17) 0.98331(13) 0.35467(12) 0.0270(4) Uani 1 1 d . . . . .
C20 C 0.46257(16) 0.87524(13) 0.33700(12) 0.0260(3) Uani 1 1 d . . . . .
C21 C 0.57748(17) 0.86226(13) 0.37265(13) 0.0278(3) Uani 1 1 d . . . . .
H21 H 0.5852 0.7933 0.3661 0.033 Uiso 1 1 calc R . . . .
C22 C 0.67787(17) 0.94838(14) 0.41652(14) 0.0304(4) Uani 1 1 d . . . . .
H22 H 0.7521 0.9371 0.4394 0.037 Uiso 1 1 calc R . . . .
C23 C 0.66934(17) 1.05442(13) 0.42728(13) 0.0289(4) Uani 1 1 d . . . . .
C24 C 0.33743(18) 0.99826(13) 0.32724(13) 0.0301(4) Uani 1 1 d . . . . .
H24 H 0.3298 1.0675 0.3357 0.036 Uiso 1 1 calc R . . . .
C25 C 0.23662(18) 0.91292(15) 0.28863(14) 0.0323(4) Uani 1 1 d . . . . .
H25 H 0.1609 0.9245 0.2743 0.039 Uiso 1 1 calc R . . . .
C26 C 0.24734(17) 0.80743(14) 0.27058(13) 0.0303(4) Uani 1 1 d . . . . .
C27 C 0.35731(17) 0.78607(13) 0.28876(12) 0.0272(3) Uani 1 1 d . . . . .
C28 C 0.88368(18) 1.12763(15) 0.50000(15) 0.0342(4) Uani 1 1 d . . . . .
H28A H 0.9055 1.0825 0.4420 0.041 Uiso 1 1 calc R . . . .
H28B H 0.8829 1.0934 0.5543 0.041 Uiso 1 1 calc R . . . .
C29 C 0.97265(18) 1.23790(15) 0.54121(15) 0.0352(4) Uani 1 1 d . . . . .
H29A H 0.9799 1.2669 0.4838 0.042 Uiso 1 1 calc R . . . .
H29B H 0.9421 1.2853 0.5906 0.042 Uiso 1 1 calc R . . . .
C30 C 1.0956(2) 1.23587(19) 0.5941(2) 0.0523(6) Uani 1 1 d . . . . .
H30A H 1.1272 1.1897 0.5444 0.063 Uiso 1 1 calc R . . . .
H30B H 1.0885 1.2060 0.6509 0.063 Uiso 1 1 calc R . . . .
C31 C 1.1824(2) 1.3475(2) 0.6364(2) 0.0577(6) Uani 1 1 d . . . . .
H31A H 1.1881 1.3780 0.5805 0.087 Uiso 1 1 calc GR . . . .
H31B H 1.2606 1.3433 0.6670 0.087 Uiso 1 1 calc GR . . . .
H31C H 1.1537 1.3922 0.6885 0.087 Uiso 1 1 calc GR . . . .
C32 C 0.54833(18) 1.18615(13) 0.41673(13) 0.0292(4) Uani 1 1 d . . . . .
H32A H 0.4845 1.1964 0.4522 0.035 Uiso 1 1 calc R . . . .
H32B H 0.6234 1.2370 0.4602 0.035 Uiso 1 1 calc R . . . .
C33 C 0.51669(17) 1.30179(13) 0.30635(13) 0.0285(4) Uani 1 1 d . . . . .
C34 C 0.4767(2) 1.40067(14) 0.18118(14) 0.0360(4) Uani 1 1 d . . . . .
H34A H 0.5457 1.4621 0.2183 0.043 Uiso 1 1 calc R . . . .
H34B H 0.4055 1.4169 0.2012 0.043 Uiso 1 1 calc R . . . .
C37 C 1.1389(3) 1.1832(3) 0.3219(3) 0.0683(8) Uani 1 1 d . . . . .
C38 C 1.2238(3) 1.2877(4) 0.3375(3) 0.0869(11) Uani 1 1 d . . . . .
H38A H 1.2842 1.3067 0.4012 0.130 Uiso 1 1 calc GR . . . .
H38B H 1.1810 1.3416 0.3416 0.130 Uiso 1 1 calc GR . . . .
H38C H 1.2618 1.2830 0.2800 0.130 Uiso 1 1 calc GR . . . .
N1 N 0.52207(16) 1.20519(11) 0.31616(11) 0.0314(3) Uani 1 1 d . . . . .
H1 H 0.5094 1.1522 0.2603 0.038 Uiso 1 1 calc R . . . .
N2 N 0.49475(18) 1.30555(12) 0.20760(12) 0.0366(4) Uani 1 1 d . . . . .
H2 H 0.4912 1.2493 0.1578 0.044 Uiso 1 1 calc R . . . .
N4 N 1.0715(4) 1.1019(3) 0.3104(3) 0.0968(10) Uani 1 1 d . . . . .
O1 O 0.74709(15) 0.66731(12) -0.04819(12) 0.0457(4) Uani 1 1 d . . . . .
O2 O 0.76730(13) 1.14251(10) 0.46633(11) 0.0360(3) Uani 1 1 d . . . . .
O3 O 0.12932(13) 0.57714(12) 0.10096(11) 0.0416(3) Uani 1 1 d . . . . .
O4 O 0.13809(13) 0.72888(10) 0.23196(11) 0.0367(3) Uani 1 1 d . . . . .
O5 O 0.53331(15) 1.38172(10) 0.38316(10) 0.0378(3) Uani 1 1 d . . . . .
C35 C 0.9310(3) 1.4162(2) 0.3592(3) 0.0633(7) Uani 1 1 d . . . . .
C36 C 0.8160(3) 1.3785(2) 0.3814(3) 0.0696(8) Uani 1 1 d . . . . .
H36A H 0.7537 1.3896 0.3335 0.104 Uiso 1 1 calc GR . . . .
H36B H 0.8172 1.4175 0.4515 0.104 Uiso 1 1 calc GR . . . .
H36C H 0.8005 1.3031 0.3739 0.104 Uiso 1 1 calc GR . . . .
N5 N 1.0232(3) 1.4494(3) 0.3471(3) 0.0966(11) Uani 1 1 d . . . . .
C40 C 0.7766(5) 0.9594(3) 0.1722(3) 0.0643(10) Uani 0.85 1 d . . P D 1
H40A H 0.7682 0.9230 0.0997 0.096 Uiso 0.85 1 calc GR . P D 1
H40B H 0.7240 0.9146 0.2002 0.096 Uiso 0.85 1 calc GR . P D 1
H40C H 0.8586 0.9740 0.2096 0.096 Uiso 0.85 1 calc GR . P D 1
C41 C 0.7448(5) 1.0596(5) 0.1829(4) 0.0600(12) Uani 0.85 1 d . . P D 1
N3 N 0.7159(5) 1.1316(5) 0.1877(4) 0.0816(15) Uani 0.85 1 d . . P D 1
C4DA C 0.3992(3) 0.98000(18) 0.06845(17) 0.0547(7) Uani 1 1 d . . . . .
C9DA C 0.3982(3) 0.8697(2) 0.0601(2) 0.0626(7) Uani 1 1 d . . . . .
H9DA H 0.3411 0.8222 -0.0025 0.094 Uiso 1 1 calc GR . . . .
H9DB H 0.3756 0.8529 0.1195 0.094 Uiso 1 1 calc GR . . . .
H9DC H 0.4771 0.8611 0.0578 0.094 Uiso 1 1 calc GR . . . .
N3DA N 0.4006(3) 1.06756(15) 0.07498(16) 0.0613(6) Uani 1 1 d . . . . .
C39 C 0.742(3) 0.980(3) 0.182(2) 0.0643(10) Uani 0.15 1 d . . P E 2
H39A H 0.7162 0.9432 0.1071 0.077 Uiso 0.15 1 calc R . P E 2
H39B H 0.6817 0.9492 0.2147 0.077 Uiso 0.15 1 calc R . P E 2
Cl1 Cl 0.8966(4) 0.9642(4) 0.2376(3) 0.0621(11) Uani 0.15 1 d . . P E 2
Cl3 Cl 0.7563(14) 1.1079(9) 0.2051(11) 0.083(3) Uani 0.15 1 d . . P E 2
O6 O 0.53865(17) 0.60296(12) 0.42640(12) 0.0441(4) Uani 1 1 d . . . . .
H6A H 0.534(3) 0.541(3) 0.409(2) 0.055(8) Uiso 1 1 d . . . . .
H6B H 0.504(2) 0.611(2) 0.483(2) 0.041(6) Uiso 1 1 d . . . . .
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'
Cl Cl 0.3639 0.7018 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2 0 -7 0.1322 -2.0000 -0.0000 -7.0000 0.3421 0.8822 -0.0427
2 -1 7 0.1378 2.0000 -1.0000 7.0000 -0.3366 -0.8425 -0.0746
1 -9 3 0.1609 1.0000 -9.0000 3.0000 -0.0850 -0.0365 -1.0362
-1 9 -2 0.1590 -1.0000 9.0000 -2.0000 0.0114 -0.0586 1.0401
-3 6 -7 0.1345 -3.0000 6.0000 -7.0000 0.2227 0.7526 0.6532
7 0 -2 0.0474 7.0000 0.0000 -2.0000 0.7533 -0.5691 0.0466
-7 0 2 0.0558 -7.0000 -0.0000 2.0000 -0.7533 0.5691 -0.0466
8 -1 -2 0.0559 8.0000 -1.0000 -2.0000 0.8453 -0.6378 -0.0629
-1 7 -7 0.1209 -1.0000 7.0000 -7.0000 0.3903 0.4960 0.7861
1 3 6 0.1829 1.0000 3.0000 6.0000 -0.3715 -0.7977 0.3830
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
C2 C1 C34 120.74(18) . 2_675
C6 C1 C2 119.88(16) . .
C6 C1 C34 119.33(18) . 2_675
C1 C2 C3 120.39(18) . .
C7 C2 C1 121.83(16) . .
C7 C2 C3 117.78(17) . .
C4 C3 C2 116.90(17) . .
C4 C3 C10 122.49(15) . .
C10 C3 C2 120.61(17) . .
C3 C4 H4 118.8 . .
C5 C4 C3 122.40(16) . .
C5 C4 H4 118.8 . .
C4 C5 H5 119.9 . .
C4 C5 C6 120.25(19) . .
C6 C5 H5 119.9 . .
C1 C6 C5 120.05(18) . .
O1 C6 C1 116.87(17) . .
O1 C6 C5 123.07(19) . .
C2 C7 H7 119.4 . .
C8 C7 C2 121.30(17) . .
C8 C7 H7 119.4 . .
C7 C8 H8 120.0 . .
C7 C8 C9 120.06(19) . .
C9 C8 H8 120.0 . .
C10 C9 C8 122.09(19) . .
C10 C9 O3 124.39(17) . .
O3 C9 C8 113.52(18) . .
C3 C10 C15 123.32(16) . .
C9 C10 C3 117.96(16) . .
C9 C10 C15 118.70(17) . .
H11A C11 H11B 108.5 . .
C12 C11 H11A 110.2 . .
C12 C11 H11B 110.2 . .
O1 C11 H11A 110.2 . .
O1 C11 H11B 110.2 . .
O1 C11 C12 107.5(3) . .
C11 C12 H12 120.5 . .
C11 C12 H12A 122.3 . .
C13 C12 C11 119.1(3) . .
C13 C12 H12 120.5 . .
C13B C12 C11 115.4(3) . .
C13B C12 H12A 122.3 . .
C12 C13 H13A 107.9 . .
C12 C13 H13B 107.9 . .
C12 C13 C14 117.8(4) . .
H13A C13 H13B 107.2 . .
C14 C13 H13A 107.9 . .
C14 C13 H13B 107.9 . .
C12 C13B H13C 108.6 . .
C12 C13B H13D 108.6 . .
C12 C13B C14 114.7(4) . .
H13C C13B H13D 107.6 . .
C14 C13B H13C 108.6 . .
C14 C13B H13D 108.6 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
C13B C14 H14D 109.5 . .
C13B C14 H14E 109.5 . .
C13B C14 H14F 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
H14D C14 H14E 109.5 . .
H14D C14 H14F 109.5 . .
H14E C14 H14F 109.5 . .
C10 C15 H15 110.9 . .
C10 C15 C16 107.83(15) . .
C16 C15 H15 110.9 . .
C27 C15 C10 109.59(13) . .
C27 C15 H15 110.9 . .
C27 C15 C16 106.57(14) . .
C15 C16 H16A 110.2 . .
C15 C16 H16B 110.2 . .
H16A C16 H16B 108.5 . .
C17 C16 C15 107.57(15) . .
C17 C16 H16A 110.2 . .
C17 C16 H16B 110.2 . .
C16 C17 H17 108.0 . .
O3 C17 C16 111.63(17) . .
O3 C17 H17 108.0 . .
O3 C17 O4 108.08(16) . .
O4 C17 C16 112.91(16) . .
O4 C17 H17 108.0 . .
C19 C18 C32 120.39(16) . .
C23 C18 C19 119.45(15) . .
C23 C18 C32 120.16(16) . .
C18 C19 C20 120.66(17) . .
C24 C19 C18 121.36(15) . .
C24 C19 C20 117.98(16) . .
C21 C20 C19 117.10(15) . .
C21 C20 C27 122.66(15) . .
C27 C20 C19 120.19(16) . .
C20 C21 H21 119.0 . .
C22 C21 C20 121.90(15) . .
C22 C21 H21 119.0 . .
C21 C22 H22 119.8 . .
C21 C22 C23 120.46(17) . .
C23 C22 H22 119.8 . .
C18 C23 C22 120.18(17) . .
O2 C23 C18 117.03(15) . .
O2 C23 C22 122.79(17) . .
C19 C24 H24 119.4 . .
C25 C24 C19 121.23(16) . .
C25 C24 H24 119.4 . .
C24 C25 H25 120.0 . .
C24 C25 C26 119.97(18) . .
C26 C25 H25 120.0 . .
C27 C26 C25 122.20(17) . .
C27 C26 O4 123.95(16) . .
O4 C26 C25 113.84(17) . .
C20 C27 C15 124.53(16) . .
C26 C27 C15 117.40(16) . .
C26 C27 C20 118.05(15) . .
H28A C28 H28B 108.6 . .
C29 C28 H28A 110.3 . .
C29 C28 H28B 110.3 . .
O2 C28 H28A 110.3 . .
O2 C28 H28B 110.3 . .
O2 C28 C29 106.91(15) . .
C28 C29 H29A 109.1 . .
C28 C29 H29B 109.1 . .
H29A C29 H29B 107.8 . .
C30 C29 C28 112.45(17) . .
C30 C29 H29A 109.1 . .
C30 C29 H29B 109.1 . .
C29 C30 H30A 109.3 . .
C29 C30 H30B 109.3 . .
C29 C30 C31 111.4(2) . .
H30A C30 H30B 108.0 . .
C31 C30 H30A 109.3 . .
C31 C30 H30B 109.3 . .
C30 C31 H31A 109.5 . .
C30 C31 H31B 109.5 . .
C30 C31 H31C 109.5 . .
H31A C31 H31B 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
C18 C32 H32A 109.8 . .
C18 C32 H32B 109.8 . .
H32A C32 H32B 108.2 . .
N1 C32 C18 109.37(13) . .
N1 C32 H32A 109.8 . .
N1 C32 H32B 109.8 . .
N2 C33 N1 115.27(15) . .
O5 C33 N1 122.10(16) . .
O5 C33 N2 122.62(15) . .
C1 C34 H34A 110.0 2_675 .
C1 C34 H34B 110.0 2_675 .
H34A C34 H34B 108.4 . .
N2 C34 C1 108.38(13) . 2_675
N2 C34 H34A 110.0 . .
N2 C34 H34B 110.0 . .
N4 C37 C38 179.2(4) . .
C37 C38 H38A 109.5 . .
C37 C38 H38B 109.5 . .
C37 C38 H38C 109.5 . .
H38A C38 H38B 109.5 . .
H38A C38 H38C 109.5 . .
H38B C38 H38C 109.5 . .
C32 N1 H1 118.4 . .
C33 N1 C32 123.26(14) . .
C33 N1 H1 118.4 . .
C33 N2 C34 123.04(14) . .
C33 N2 H2 118.5 . .
C34 N2 H2 118.5 . .
C6 O1 C11 119.11(18) . .
C23 O2 C28 118.81(14) . .
C9 O3 C17 116.76(15) . .
C26 O4 C17 118.94(16) . .
N5 C35 C36 176.3(4) . .
C35 C36 H36A 109.5 . .
C35 C36 H36B 109.5 . .
C35 C36 H36C 109.5 . .
H36A C36 H36B 109.5 . .
H36A C36 H36C 109.5 . .
H36B C36 H36C 109.5 . .
H40A C40 H40B 109.5 . .
H40A C40 H40C 109.5 . .
H40B C40 H40C 109.5 . .
C41 C40 H40A 109.5 . .
C41 C40 H40B 109.5 . .
C41 C40 H40C 109.5 . .
N3 C41 C40 176.6(6) . .
N3DA C4DA C9DA 179.7(3) . .
C4DA C9DA H9DA 109.5 . .
C4DA C9DA H9DB 109.5 . .
C4DA C9DA H9DC 109.5 . .
H9DA C9DA H9DB 109.5 . .
H9DA C9DA H9DC 109.5 . .
H9DB C9DA H9DC 109.5 . .
H39A C39 H39B 108.5 . .
Cl1 C39 H39A 110.3 . .
Cl1 C39 H39B 110.3 . .
Cl3 C39 H39A 110.3 . .
Cl3 C39 H39B 110.3 . .
Cl3 C39 Cl1 107(2) . .
H6A O6 H6B 103(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.423(3) .
C1 C6 1.378(3) .
C1 C34 1.509(2) 2_675
C2 C3 1.433(2) .
C2 C7 1.421(3) .
C3 C4 1.410(3) .
C3 C10 1.432(3) .
C4 H4 0.9300 .
C4 C5 1.368(3) .
C5 H5 0.9300 .
C5 C6 1.412(3) .
C6 O1 1.368(2) .
C7 H7 0.9300 .
C7 C8 1.360(3) .
C8 H8 0.9300 .
C8 C9 1.415(3) .
C9 C10 1.372(3) .
C9 O3 1.383(2) .
C10 C15 1.531(2) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 C12 1.515(3) .
C11 O1 1.432(3) .
C12 H12 0.9300 .
C12 H12A 0.9300 .
C12 C13 1.379(6) .
C12 C13B 1.361(6) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C13 C14 1.525(7) .
C13B H13C 0.9700 .
C13B H13D 0.9700 .
C13B C14 1.589(7) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C14 H14D 0.9600 .
C14 H14E 0.9600 .
C14 H14F 0.9600 .
C15 H15 0.9800 .
C15 C16 1.533(2) .
C15 C27 1.527(2) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C16 C17 1.507(3) .
C17 H17 0.9800 .
C17 O3 1.418(2) .
C17 O4 1.422(2) .
C18 C19 1.426(2) .
C18 C23 1.382(3) .
C18 C32 1.511(2) .
C19 C20 1.435(2) .
C19 C24 1.418(3) .
C20 C21 1.415(3) .
C20 C27 1.432(2) .
C21 H21 0.9300 .
C21 C22 1.371(3) .
C22 H22 0.9300 .
C22 C23 1.417(2) .
C23 O2 1.366(2) .
C24 H24 0.9300 .
C24 C25 1.365(3) .
C25 H25 0.9300 .
C25 C26 1.407(3) .
C26 C27 1.374(3) .
C26 O4 1.384(2) .
C28 H28A 0.9700 .
C28 H28B 0.9700 .
C28 C29 1.510(3) .
C28 O2 1.436(2) .
C29 H29A 0.9700 .
C29 H29B 0.9700 .
C29 C30 1.507(3) .
C30 H30A 0.9700 .
C30 H30B 0.9700 .
C30 C31 1.514(3) .
C31 H31A 0.9600 .
C31 H31B 0.9600 .
C31 H31C 0.9600 .
C32 H32A 0.9700 .
C32 H32B 0.9700 .
C32 N1 1.458(2) .
C33 N1 1.349(2) .
C33 N2 1.347(2) .
C33 O5 1.240(2) .
C34 C1 1.509(2) 2_675
C34 H34A 0.9700 .
C34 H34B 0.9700 .
C34 N2 1.460(2) .
C37 C38 1.468(6) .
C37 N4 1.152(5) .
C38 H38A 0.9600 .
C38 H38B 0.9600 .
C38 H38C 0.9600 .
N1 H1 0.8600 .
N2 H2 0.8600 .
C35 C36 1.440(4) .
C35 N5 1.130(4) .
C36 H36A 0.9600 .
C36 H36B 0.9600 .
C36 H36C 0.9600 .
C40 H40A 0.9600 .
C40 H40B 0.9600 .
C40 H40C 0.9600 .
C40 C41 1.448(7) .
C41 N3 1.080(8) .
C4DA C9DA 1.449(3) .
C4DA N3DA 1.149(3) .
C9DA H9DA 0.9600 .
C9DA H9DB 0.9600 .
C9DA H9DC 0.9600 .
C39 H39A 0.9700 .
C39 H39B 0.9700 .
C39 Cl1 1.92(3) .
C39 Cl3 1.62(3) .
O6 H6A 0.78(3) .
O6 H6B 0.92(3) .
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
C1 C2 C3 C4 -2.2(2) . . . .
C1 C2 C3 C10 178.27(14) . . . .
C1 C2 C7 C8 178.31(17) . . . .
C1 C6 O1 C11 -178.28(18) . . . .
C1 C34 N2 C33 176.77(19) 2_675 . . .
C2 C1 C6 C5 3.2(3) . . . .
C2 C1 C6 O1 -177.55(14) . . . .
C2 C3 C4 C5 1.9(2) . . . .
C2 C3 C10 C9 4.6(2) . . . .
C2 C3 C10 C15 -173.72(14) . . . .
C2 C7 C8 C9 2.2(3) . . . .
C3 C2 C7 C8 -2.2(3) . . . .
C3 C4 C5 C6 0.9(3) . . . .
C3 C10 C15 C16 -152.64(16) . . . .
C3 C10 C15 C27 91.74(19) . . . .
C4 C3 C10 C9 -174.94(16) . . . .
C4 C3 C10 C15 6.8(2) . . . .
C4 C5 C6 C1 -3.6(3) . . . .
C4 C5 C6 O1 177.27(16) . . . .
C5 C6 O1 C11 0.9(3) . . . .
C6 C1 C2 C3 -0.3(2) . . . .
C6 C1 C2 C7 179.09(16) . . . .
C7 C2 C3 C4 178.35(15) . . . .
C7 C2 C3 C10 -1.2(2) . . . .
C7 C8 C9 C10 1.4(3) . . . .
C7 C8 C9 O3 -179.38(17) . . . .
C8 C9 C10 C3 -4.7(3) . . . .
C8 C9 C10 C15 173.64(16) . . . .
C8 C9 O3 C17 -168.75(17) . . . .
C9 C10 C15 C16 29.1(2) . . . .
C9 C10 C15 C27 -86.55(19) . . . .
C10 C3 C4 C5 -178.55(15) . . . .
C10 C9 O3 C17 10.4(3) . . . .
C10 C15 C16 C17 -56.06(19) . . . .
C10 C15 C27 C20 -99.53(19) . . . .
C10 C15 C27 C26 78.65(19) . . . .
C11 C12 C13 C14 -63.9(6) . . . .
C11 C12 C13B C14 73.5(5) . . . .
C12 C11 O1 C6 -177.6(2) . . . .
C15 C16 C17 O3 64.03(19) . . . .
C15 C16 C17 O4 -58.0(2) . . . .
C16 C15 C27 C20 144.06(16) . . . .
C16 C15 C27 C26 -37.77(19) . . . .
C16 C17 O3 C9 -40.1(2) . . . .
C16 C17 O4 C26 26.5(2) . . . .
C18 C19 C20 C21 4.3(2) . . . .
C18 C19 C20 C27 -178.03(13) . . . .
C18 C19 C24 C25 -176.97(15) . . . .
C18 C23 O2 C28 177.47(15) . . . .
C18 C32 N1 C33 -175.01(17) . . . .
C19 C18 C23 C22 -3.6(2) . . . .
C19 C18 C23 O2 177.57(14) . . . .
C19 C18 C32 N1 -71.0(2) . . . .
C19 C20 C21 C22 -3.9(2) . . . .
C19 C20 C27 C15 171.41(14) . . . .
C19 C20 C27 C26 -6.8(2) . . . .
C19 C24 C25 C26 -3.1(3) . . . .
C20 C19 C24 C25 2.3(2) . . . .
C20 C21 C22 C23 -0.2(3) . . . .
C21 C20 C27 C15 -11.0(2) . . . .
C21 C20 C27 C26 170.79(15) . . . .
C21 C22 C23 C18 4.1(3) . . . .
C21 C22 C23 O2 -177.16(15) . . . .
C22 C23 O2 C28 -1.3(2) . . . .
C23 C18 C19 C20 -0.6(2) . . . .
C23 C18 C19 C24 178.62(15) . . . .
C23 C18 C32 N1 108.81(18) . . . .
C24 C19 C20 C21 -174.98(14) . . . .
C24 C19 C20 C27 2.7(2) . . . .
C24 C25 C26 C27 -1.2(3) . . . .
C24 C25 C26 O4 179.68(15) . . . .
C25 C26 C27 C15 -172.23(15) . . . .
C25 C26 C27 C20 6.1(2) . . . .
C25 C26 O4 C17 179.22(15) . . . .
C27 C15 C16 C17 61.53(18) . . . .
C27 C20 C21 C22 178.49(15) . . . .
C27 C26 O4 C17 0.1(2) . . . .
C28 C29 C30 C31 -179.0(2) . . . .
C29 C28 O2 C23 -178.66(15) . . . .
C32 C18 C19 C20 179.19(14) . . . .
C32 C18 C19 C24 -1.6(2) . . . .
C32 C18 C23 C22 176.59(14) . . . .
C32 C18 C23 O2 -2.2(2) . . . .
C34 C1 C2 C3 -177.72(14) 2_675 . . .
C34 C1 C2 C7 1.7(2) 2_675 . . .
C34 C1 C6 C5 -179.35(15) 2_675 . . .
C34 C1 C6 O1 -0.1(2) 2_675 . . .
N1 C33 N2 C34 175.22(19) . . . .
N2 C33 N1 C32 178.19(18) . . . .
O1 C11 C12 C13 152.2(4) . . . .
O1 C11 C12 C13B 87.8(4) . . . .
O2 C28 C29 C30 171.41(18) . . . .
O3 C9 C10 C3 176.17(15) . . . .
O3 C9 C10 C15 -5.5(3) . . . .
O3 C17 O4 C26 -97.50(19) . . . .
O4 C17 O3 C9 84.7(2) . . . .
O4 C26 C27 C15 6.8(2) . . . .
O4 C26 C27 C20 -174.90(14) . . . .
O5 C33 N1 C32 -0.4(3) . . . .
O5 C33 N2 C34 -6.2(3) . . . .
