Bis-urea macrocycles with a deep cavity
Guobao Huang; Zhenfeng He; Chen-Xi Cai; Fangfang Pan; Dingqiao Yang; Kari Rissanen; Wei Jiang; Chem.Commun. 51 (2015) 15490–; doi:10.1039/C5cc06768E

data_7117966
_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       '\w 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/[\s^2^(Fo^2^)+(0.1314P)^2^+0.6904P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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
_chemical_oxdiff_formula         'C80 H100 O20 Cl2'
_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'