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_7117967
_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 H72 N4 O10, 2.5(C4 H6 N2), C H2 Cl2, 2(H2 O)'
_chemical_formula_sum            'C79 H93 Cl2 N9 O12'
_chemical_formula_weight         1431.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   other
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.8532(2)
_cell_length_b                   16.58652(16)
_cell_length_c                   19.13712(18)
_cell_measurement_reflns_used    10737
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      76.2190
_cell_measurement_theta_min      3.5040
_cell_volume                     7571.44(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      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega   87.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   90.0000 91

  2 omega   54.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 43

  3 omega   52.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 39

  4 omega   42.00   99.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -30.0000 57

  5 omega   39.00  139.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -150.0000 100

  6 omega   37.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 48

  7 omega  -36.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000 -120.0000 68

  8 omega  -28.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000    0.0000 61

  9 omega  -49.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000  120.0000 82
;
_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      0.0540203000
_diffrn_orient_matrix_UB_12      0.0437204000
_diffrn_orient_matrix_UB_13      -0.0226463000
_diffrn_orient_matrix_UB_21      -0.0322841000
_diffrn_orient_matrix_UB_22      0.0412142000
_diffrn_orient_matrix_UB_23      -0.0598714000
_diffrn_orient_matrix_UB_31      -0.0145858000
_diffrn_orient_matrix_UB_32      0.0708068000
_diffrn_orient_matrix_UB_33      0.0488084000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26183
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.861
_diffrn_reflns_theta_min         3.526
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.313
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.962
_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       plate
_exptl_crystal_F_000             3040
_exptl_crystal_size_max          0.2921
_exptl_crystal_size_mid          0.2458
_exptl_crystal_size_min          0.1008
_refine_diff_density_max         1.163
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     627
_refine_ls_number_reflns         8120
_refine_ls_number_restraints     62
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0682
_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^)+(0.1189P)^2^+4.8315P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1940
_refine_ls_wR_factor_ref         0.2042
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                6922
_reflns_number_total             8120
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc06768e2.cif
_cod_data_source_block           acn@1-syn
_cod_original_cell_volume        7571.45(12)
_cod_database_code               7117967
_chemical_oxdiff_formula         'C80 H10 O20 N2'
_reflns_odcompleteness_completeness 99.77
_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
2. Restrained distances
 N6-C44
 1.15 with sigma of 0.01
 C44-C43
 1.45 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C45B) \\sim Ueq, Uanis(C46B) \\sim Ueq, Uanis(N7B) \\sim Ueq, Uanis(C45)
\\sim Ueq, Uanis(N7) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C36) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N6) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C43) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: H12A(0.5) H12B(0.5) H31A(0.5) H31B(0.5) C33(0.5) H33A(0.5)
 H33B(0.5) C33B(0.5) H33C(0.5) H33D(0.5) C34(0.5) H34A(0.5) H34B(0.5) C34B(0.5)
 H34C(0.5) H34D(0.5) C35(0.5) H35A(0.5) H35B(0.5) C35B(0.5) H35C(0.5) H35D(0.5)
 C36(0.5) H36A(0.5) H36B(0.5) H36C(0.5) C36B(0.5) H36D(0.5) H36E(0.5) H36F(0.5)
 O3(0.5) O3B(0.5) O5(0.5) O5B(0.5) H43A(0.5) H43B(0.5) H43C(0.5) H47A(0.5)
 H47B(0.5) Cl2(0.25) Cl2B(0.25) C45B(0.23) H45A(0.23) H45B(0.23) H45C(0.23)
 C46B(0.23) N7B(0.23) H41A(0.5) H41B(0.5) H41C(0.5) C37(0.5) C38(0.5) H38A(0.5)
 H38B(0.5) H38C(0.5) N3(0.5) C45(0.27) H45D(0.27) H45E(0.27) H45F(0.27)
 C46(0.27) N7(0.27) C39(0.5) C40(0.5) H40A(0.5) H40B(0.5) H40C(0.5) N4(0.5)
 Fixed X: N7B(0.95516)
 Fixed Y: C45B(0.25) C46B(0.25) N7B(0.25)
 Fixed Z: N7B(0.22208)
5.a Riding coordinates:
 C43(H43A,H43B,H43C)
5.b Ternary CH refined with riding coordinates:
 C11(H11), C13(H13), C30(H30), C32(H32)
5.c Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,
 H18B), C20(H20A,H20B), C31(H31A,H31B), C33(H33A,H33B), C33B(H33C,H33D),
 C34(H34A,H34B), C34B(H34C,H34D), C35(H35A,H35B), C35B(H35C,H35D), C47(H47A,
 H47B)
5.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C24(H24), C25(H25), C26(H26), C27(H27),
 N1(H1), N2(H2)
5.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C36(H36A,H36B,H36C), C36B(H36D,H36E,H36F), C45B(H45A,
 H45B,H45C), C41(H41A,H41B,H41C), C38(H38A,H38B,H38C), C45(H45D,H45E,H45F),
 C40(H40A,H40B,H40C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'