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_7220273
_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         'C52 H68 O14, C H2 Cl2, C H4 O'
_chemical_formula_sum            'C54 H74 Cl2 O15'
_chemical_formula_weight         1034.03
_chemical_name_common
'C-methyl tetramethoxy resorcinarene bis-crown-5 dichloromethane methanol solvate'
_chemical_name_systematic
'C-methyl tetramethoxy resorcinarene bis-crown-5 dichloromethane methanol solvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-01-29
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_audit_update_record
;
2015-01-05 deposited with the CCDC.
2015-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.1831(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.9718(4)
_cell_length_b                   19.3215(3)
_cell_length_c                   15.5981(2)
_cell_measurement_reflns_used    8086
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.8090
_cell_measurement_theta_min      4.0930
_cell_volume                     5294.33(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector_area_resol_mean 5.1977
_diffrn_measured_fraction_theta_full 0.9834
_diffrn_measured_fraction_theta_max 0.9464
_diffrn_measurement_details
;
  1 omega  -49.00   33.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4013   37.0000  -30.0000 82

  2 omega  -74.00   35.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4013   77.0000 -150.0000 109

  3 omega   30.00   91.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -30.0000   30.0000 61

  4 omega   41.00  117.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601 -125.0000  -90.0000 76

  5 omega   40.00  105.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000   90.0000 65

  6 omega   38.00   91.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -30.0000  -30.0000 53

  7 omega   30.00   77.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -30.0000  -60.0000 47

  8 omega   94.00  174.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  125.0000   90.0000 80
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0559783000
_diffrn_orient_matrix_UB_12      -0.0612090000
_diffrn_orient_matrix_UB_13      -0.0165320000
_diffrn_orient_matrix_UB_21      0.0667566000
_diffrn_orient_matrix_UB_22      -0.0502248000
_diffrn_orient_matrix_UB_23      0.0003525000
_diffrn_orient_matrix_UB_31      0.0092459000
_diffrn_orient_matrix_UB_32      -0.0099637000
_diffrn_orient_matrix_UB_33      0.0996990000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            17795
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.229
_diffrn_reflns_theta_min         3.400
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       plate
_exptl_crystal_F_000             2208
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/methanol'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.504
_refine_diff_density_min         -1.203
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     713
_refine_ls_number_reflns         10237
_refine_ls_number_restraints     67
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0932
_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^)+(0.1903P)^2^+5.3916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2789
_refine_ls_wR_factor_ref         0.2996
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7796
_reflns_number_total             10237
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ce00311c2.cif
_cod_data_source_block           1-IV
_cod_depositor_comments
'Adding full bibliography for 7220270--7220279.cif.'
_cod_original_cell_volume        5294.30(16)
_cod_database_code               7220273
_reflns_odcompleteness_completeness 98.34
_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 C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 Cl1-C102 = Cl2A-C102 = Cl2-C102
 1.79 with sigma of 0.02
 O53-C52A \\sim O53-C52
 with sigma of 0.02
 O18-C48 \\sim O18-C48A
 with sigma of 0.02
 C49-C48 \\sim C49A-C48A
 with sigma of 0.02
 O50-C49 \\sim O50A-C49A
 with sigma of 0.02
 O42-C41 \\sim O42A-C41
 with sigma of 0.02
 O42-C43 \\sim O42A-C43A
 with sigma of 0.02
 C52A-C51A \\sim C52-C51
 with sigma of 0.02
 O50A-C51A \\sim O50-C51
 with sigma of 0.02
3. Rigid bond restraints
 O50A, O50
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O42, O42A, C43, C43A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C51A, C51
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C48, C48A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O50A \\sim O50: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
O42 \\sim O42A \\sim C43 \\sim C43A: within 1.7A with sigma of 0.04 and sigma 
for terminal atoms of 0.08
C51 \\sim C51A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 
0.08
C48 \\sim C48A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 
0.08
Uanis(Cl2) = Uanis(Cl2A)
Uanis(O42A) = Uanis(O42)
5. Others
 Sof(O50A)=Sof(C48A)=Sof(H48C)=Sof(H48D)=Sof(C49A)=Sof(H49C)=Sof(H49D)=
 Sof(C51A)=Sof(H51C)=Sof(H51D)=Sof(C52A)=Sof(H52C)=Sof(H52D)=1-FVAR(1)
 Sof(O50)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(C51)=
 Sof(H51A)=Sof(H51B)=Sof(C52)=Sof(H52A)=Sof(H52B)=FVAR(1)
 Sof(O42A)=Sof(H41C)=Sof(H41D)=Sof(C43A)=Sof(H43C)=Sof(H43D)=Sof(H44C)=
 Sof(H44D)=1-FVAR(2)
 Sof(O42)=Sof(H41A)=Sof(H41B)=Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(H44A)=Sof(H44B)=
 FVAR(2)
 Sof(Cl2A)=Sof(H10C)=Sof(H10D)=1-FVAR(3)
 Sof(Cl2)=Sof(H10A)=Sof(H10B)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C21(H21), C28(H28)
6.b Secondary CH2 refined with riding coordinates:
 C102(H10A,H10B), C102(H10C,H10D), C37(H37A,H37B), C38(H38A,H38B), C40(H40A,
 H40B), C41(H41A,H41B), C41(H41C,H41D), C43(H43A,H43B), C43A(H43C,H43D),
 C44(H44A,H44B), C44(H44C,H44D), C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B),
  C48A(H48C,H48D), C49(H49A,H49B), C49A(H49C,H49D), C51(H51A,H51B), C51A(H51C,
 H51D), C52(H52A,H52B), C52A(H52C,H52D), C54(H54A,H54B), C55(H55A,H55B),
 C57(H57A,H57B), C58(H58A,H58B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C9(H9), C12(H12), C16(H16), C19(H19), C23(H23), C26(H26)
6.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), C101(H10E,H10F,H10G)
6.e Idealised tetrahedral OH refined as rotating group:
 O100(H100)
;
_shelx_res_checksum              89546
_shelxl_version_number           2013-4