Influence of lower rim C-methyl group on crystal forms and metal complexation of resorcinarene bis-crown-5
Helttunen, Kaisa; Tero, Tiia-Riikka; Nissinen, Maija; CrystEngComm 17 (2015) 3667–; doi:10.1039/C5CE00311C

data_7220278
_publ_section_title
;
 Influence of lower rim C-methyl group on crystal forms and metal
 complexation of resorcinarene bis-crown-5
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              3667
_journal_paper_doi               10.1039/C5CE00311C
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C44 H54 O11, 0.5(C H Cl3), H2 O'
_chemical_formula_sum            'C44.5 H56 Cl1.5 D0.5 O12'
_chemical_formula_weight         837.08
_chemical_name_common
'C-methyl tetramethoxy resorcinarene mono-crown-5 chloroform solvate monohydrate'
_chemical_name_systematic
'C-methyl tetramethoxy resorcinarene mono-crown-5 chloroform solvate monohydrate'
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_audit_update_record
;
2015-01-05 deposited with the CCDC.
2015-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                94.688(3)
_cell_angle_beta                 95.580(3)
_cell_angle_gamma                117.328(4)
_cell_formula_units_Z            4
_cell_length_a                   15.8050(7)
_cell_length_b                   16.2661(7)
_cell_length_c                   18.4549(6)
_cell_measurement_reflns_used    6600
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      74.4666
_cell_measurement_theta_min      3.0873
_cell_volume                     4151.9(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 0.9893
_diffrn_measured_fraction_theta_max 0.9879
_diffrn_measurement_details
;
  1 omega -113.00  -16.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.9459  -57.0000  -90.0000 194

  2 omega    1.00   83.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       42.9459  -99.0000  150.0000 164

  3 omega  -56.00   28.00   0.5000   43.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   45.0000   60.0000 168

  4 omega   98.00  170.00   0.5000   43.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7406  125.0000   30.0000 144

  5 omega   35.00   82.00   0.5000   43.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7406  -30.0000  -60.0000 94

  6 omega   44.00  122.00   0.5000   43.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7406 -125.0000   90.0000 156

  7 omega   33.00   87.00   0.5000   43.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7406  -30.0000 -120.0000 108

  8 omega   39.00  120.00   0.5000   43.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7406 -125.0000  -90.0000 162

  9 omega   69.00  169.00   0.5000   43.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7406   15.0000  150.0000 200

 10 omega   46.00  103.00   0.5000   43.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7406  -94.0000  -30.0000 114

 11 omega   87.00  178.00   0.5000   43.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7406   45.0000 -150.0000 182

 12 omega   37.00  134.00   0.5000   43.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7406  -61.0000   60.0000 194
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0693053000
_diffrn_orient_matrix_UB_12      0.0422996000
_diffrn_orient_matrix_UB_13      -0.0083037000
_diffrn_orient_matrix_UB_21      0.0830338000
_diffrn_orient_matrix_UB_22      0.0921846000
_diffrn_orient_matrix_UB_23      -0.0147058000
_diffrn_orient_matrix_UB_31      -0.0250165000
_diffrn_orient_matrix_UB_32      -0.0362646000
_diffrn_orient_matrix_UB_33      -0.0830447000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25968
_diffrn_reflns_theta_full        74.64
_diffrn_reflns_theta_max         74.64
_diffrn_reflns_theta_min         3.09
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.642
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1780
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CDCl3'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.899
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1241
_refine_ls_number_reflns         16157
_refine_ls_number_restraints     79
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0744
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1353P)^2^+1.5669P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2054
_refine_ls_wR_factor_ref         0.2335
_reflns_number_gt                11657
_reflns_number_total             16157
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce00311c2.cif
_cod_data_source_block           2-I
_cod_depositor_comments
'Adding full bibliography for 7220270--7220279.cif.'
_cod_original_formula_sum        'C44.50 H56 Cl1.50 D0.50 O12'
_cod_database_code               7220278
_reflns_odcompleteness_completeness 98.93
_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 O(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl3B-C1A = Cl2B-C1A = Cl1B-C1A = Cl2-C100 = Cl1-C100 = Cl3-C100
 1.79 with sigma of 0.02
 O11-C47 = O11-C47B
 1.43 with sigma of 0.02
 C47B-C46B
 1.54 with sigma of 0.02
 O70-H70 = O18-H18 = O25-H25 = O63-H63
 0.82 with sigma of 0.02
 O105-H10C = O105-H10D = O104-H10B = O104-H10A
 0.82 with sigma of 0.02
 O42-C43 \\sim O42B-C43
 with sigma of 0.02
 O42-C41 \\sim O42B-C41B
 with sigma of 0.02
 C41-C40 \\sim C40B-C41B
 with sigma of 0.02
 O39-C40B \\sim O39-C40
 with sigma of 0.02
 O92-C93 \\sim O92B-C93
 with sigma of 0.02
 O92B-C91B \\sim O92-C91
 with sigma of 0.02
 C90B-C91B \\sim C91-C90
 with sigma of 0.02
 O95B-C94B \\sim O95-C94
 with sigma of 0.02
 O77-C97 \\sim O77-C97B
 with sigma of 0.02
 C97B-C96B \\sim C97-C96
 with sigma of 0.02
 O95B-C96B \\sim O95-C96
 with sigma of 0.02
 C43-C44 \\sim C43B-C44B
 with sigma of 0.02
 O45-C44 \\sim O45B-C44B
 with sigma of 0.02
 O45B-C46B \\sim O45-C46
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C97B) \\sim Ueq, Uanis(C93B) \\sim Ueq, Uanis(O92B) \\sim Ueq,
Uanis(O95B) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C44B) \\sim Ueq, Uanis(C43B) \\sim Ueq, Uanis(O45B) \\sim Ueq,
Uanis(C46B) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C40) = Uanis(C40B)
Uanis(C90) = Uanis(C90B)
Uanis(C47B) = Uanis(C47)
Uanis(C44B) = Uanis(O45B)
4. Others
 Fixed Sof: Cl1(0.8) Cl1B(0.2) Cl2(0.8) Cl2B(0.2) Cl3(0.8) Cl3B(0.2) O42(0.8)
 O42B(0.2) O45(0.8) O45B(0.2) O92(0.8) O92B(0.2) O95(0.8) O95B(0.2) C1A(0.2)
 H1A(0.2) C40(0.8) H40A(0.8) H40B(0.8) C40B(0.2) H40C(0.2) H40D(0.2) C41(0.8)
 H41A(0.8) H41B(0.8) C41B(0.2) H41C(0.2) H41D(0.2) C43(0.8) H43A(0.8) H43B(0.8)
 C43B(0.2) H43C(0.2) H43D(0.2) C44(0.8) H44A(0.8) H44B(0.8) C44B(0.2) H44C(0.2)
 H44D(0.2) C46(0.8) H46A(0.8) H46B(0.8) C46B(0.2) H46C(0.2) H46D(0.2) C47(0.8)
 H47A(0.8) H47B(0.8) C47B(0.2) H47C(0.2) H47D(0.2) C90(0.8) H90A(0.8) H90B(0.8)
 C90B(0.2) H90C(0.2) H90D(0.2) C91(0.8) H91A(0.8) H91B(0.8) C91B(0.2) H91C(0.2)
 H91D(0.2) C93(0.8) H93A(0.8) H93B(0.8) C93B(0.2) H93C(0.2) H93D(0.2) C94(0.8)
 H94A(0.8) H94B(0.8) C94B(0.2) H94C(0.2) H94D(0.2) C96(0.8) H96A(0.8) H96B(0.8)
 C96B(0.2) H96C(0.2) H96D(0.2) C97(0.8) H97A(0.8) H97B(0.8) C97B(0.2) H97C(0.2)
 H97D(0.2) C100(0.8) H100(0.8)
5.a Ternary CH refined with riding coordinates:
 C1A(H1A), C7(H7), C14(H14), C21(H21), C28(H28), C57(H57), C64(H64), C71(H71),
 C78(H78), C100(H100)
5.b Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C38(H38A,H38B), C40(H40A,H40B), C40B(H40C,H40D), C41(H41A,
 H41B), C41B(H41C,H41D), C43(H43A,H43B), C43B(H43C,H43D), C44(H44A,H44B),
 C44B(H44C,H44D), C46(H46A,H46B), C46B(H46C,H46D), C47(H47A,H47B), C47B(H47C,
 H47D), C87(H87A,H87B), C88(H88A,H88B), C90(H90A,H90B), C90B(H90C,H90D),
 C91(H91A,H91B), C91B(H91C,H91D), C93(H93A,H93B), C93B(H93C,H93D), C94(H94A,
 H94B), C94B(H94C,H94D), C96(H96A,H96B), C96B(H96C,H96D), C97(H97A,H97B),
 C97B(H97C,H97D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C9(H9), C12(H12), C16(H16), C19(H19), C23(H23), C26(H26),
 C52(H52), C55(H55), C59(H59), C62(H62), C66(H66), C69(H69), C73(H73), C76(H76)
5.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,
 H36B,H36C), C79(H79A,H79B,H79C), C80(H80A,H80B,H80C), C81(H81A,H81B,H81C),
 C82(H82A,H82B,H82C), C83(H83A,H83B,H83C), C84(H84A,H84B,H84C), C85(H85A,H85B,
 H85C), C86(H86A,H86B,H86C)
;
_shelx_res_checksum              66487