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_7117969
_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
'1.4(C H2 Cl2), 2.6(C4 H8 O2), C68 H72 N4 O10'
_chemical_formula_sum            'C79.8 H95.6 Cl2.8 N4 O15.2'
_chemical_formula_weight         1453.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-08-08
_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                90
_cell_angle_beta                 96.545(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.4884(7)
_cell_length_b                   17.1551(9)
_cell_length_c                   17.3844(8)
_cell_measurement_reflns_used    6236
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.6420
_cell_measurement_theta_min      3.5660
_cell_volume                     3700.2(3)
_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_temperature      100.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -37.00   48.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.7586   57.0000 -150.0000 85

  2 omega  -47.00   53.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.7586   77.0000  -60.0000 100

  3 omega   -3.00   87.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9305   57.0000 -150.0000 90

  4 omega    7.00   80.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9305 -133.0000   49.2284 73

  5 omega  -50.00   39.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9305  -57.0000   90.0000 89

  6 omega    2.00   87.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9305   57.0000   90.0000 85

  7 omega   26.00   76.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9305   37.0000  -90.0000 50

  8 omega  -12.00   75.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9305   77.0000  -30.0000 87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0404208000
_diffrn_orient_matrix_UB_12      0.0034064000
_diffrn_orient_matrix_UB_13      0.0253512000
_diffrn_orient_matrix_UB_21      -0.0073489000
_diffrn_orient_matrix_UB_22      -0.0410226000
_diffrn_orient_matrix_UB_23      -0.0011091000
_diffrn_orient_matrix_UB_31      0.0397342000
_diffrn_orient_matrix_UB_32      -0.0040148000
_diffrn_orient_matrix_UB_33      0.0322849000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            42494
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         2.887
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.974
_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    1.304
_exptl_crystal_description       plate
_exptl_crystal_F_000             1543
_exptl_crystal_size_max          0.5527
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         6696
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0763
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1042P)^2^+2.1619P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1857
_refine_ls_wR_factor_ref         0.2193
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4270
_reflns_number_total             6696
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc06768e2.cif
_cod_data_source_block           4@1-syn
_cod_original_formula_sum        'C79.80 H95.60 Cl2.80 N4 O15.20'
_cod_database_code               7117969
_chemical_oxdiff_formula         'C40 H40 O8 N4'
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C42-C38
 1.52 with sigma of 0.01
 H28A_$1-H32A
 2.2 with sigma of 0.01
 C44-Cl3 \\sim C44-Cl4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C39) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C33B) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(Cl3) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(Cl4) \\sim Ueq, Uanis(O10)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C44) = Uanis(C38)
4. Others
 Sof(Cl2)=1-FVAR(1)
 Sof(H40C)=Sof(H40D)=0.5*(1-FVAR(2))
 Sof(H40A)=Sof(H40B)=0.5*FVAR(2)
 Sof(Cl1)=FVAR(1)
 Fixed Sof: H31A(0.75) H31B(0.75) H31C(0.25) H31D(0.25) C32(0.75) H32A(0.75)
 H32B(0.75) C33(0.75) H33A(0.75) H33B(0.75) H33C(0.75) O11(0.8) O10(0.8)
 C36(0.8) H36A(0.8) H36B(0.8) C38(0.8) H38A(0.8) H38B(0.8) C32B(0.25)
 H32C(0.25) H32D(0.25) C33B(0.25) H33D(0.25) H33E(0.25) H33F(0.25) Cl4(0.2)
 C39(0.8) H39A(0.8) H39B(0.8) C42(0.8) H42A(0.8) H42B(0.8) Cl3(0.2) C44(0.2)
 H44A(0.2) H44B(0.2)
5.a Ternary CH refined with riding coordinates:
 C43(H43), C24(H24)
5.b Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B), C40(H40C,H40D), C34(H34A,H34B), C35(H35A,H35B), C11(H11A,
 H11B), C13(H13A,H13B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B),
 C28(H28A,H28B), C30(H30A,H30B), C31(H31A,H31B), C31(H31C,H31D), C32(H32A,H32B),
  C36(H36A,H36B), C38(H38A,H38B), C32B(H32C,H32D), C39(H39A,H39B), C42(H42A,
 H42B), C44(H44A,H44B)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C3(H3A), C4(H4), C0AA(H0AA), C1AA(H1AA), C16(H16), C17(H17),
 C20(H20), C21(H21)
5.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C33(H33A,H33B,H33C), C33B(H33D,H33E,H33F)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'