2-Methylresorcinarene: a very high packing coefficient in a mono-anion based dimeric capsule and the X-ray crystal structure of the tetra-anion.
Puttreddy, Rakesh; Beyeh, Ngong Kodiah; Kalenius, Elina; Ras, Robin H. A.; Rissanen, Kari; Chemical communications (Cambridge, England) 52 (2016) 8115–8118; doi:10.1039/c6cc03289c

data_7124663
_publ_section_title
;
 2-Methylresorcinarene: a very high packing coefficient in a mono-anion
 based dimeric capsule and the X-ray crystal structure of the tetra-anion.
;
_journal_issue                   52
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8115
_journal_page_last               8118
_journal_paper_doi               10.1039/c6cc03289c
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety
'15(C H4 O), 0.5(H2 O), 2(C40 H44 O8), 3(C6 H16 N2), 2(C6 H15 N2)'
_chemical_formula_sum            'C125 H227 N10 O31.5'
_chemical_formula_weight         2374.15
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-04-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-04-10 deposited with the CCDC.
2016-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                69.234(6)
_cell_angle_beta                 75.125(6)
_cell_angle_gamma                87.036(5)
_cell_formula_units_Z            1
_cell_length_a                   13.3506(9)
_cell_length_b                   15.7389(11)
_cell_length_c                   17.8889(12)
_cell_measurement_reflns_used    8366
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.3610
_cell_measurement_theta_min      2.1290
_cell_volume                     3393.7(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      170
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -94.00  -35.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368 -178.0000  -60.0000 59

  2 omega  -11.00   89.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2305   77.0000  -30.0000 100

  3 omega    3.00   77.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2305 -126.0000  109.0000 74

  4 omega  -51.00   49.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2305  -77.0000 -150.0000 100

  5 omega   -2.00   88.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2305   57.0000 -150.0000 90

  6 omega  -25.00   92.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2305   19.0000  150.0000 117

  7 omega  -44.00   -7.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368   37.0000  120.0000 37

  8 omega  -94.00  -35.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368 -178.0000 -150.0000 59
;
_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      -0.0114640000
_diffrn_orient_matrix_UB_12      -0.0384709000
_diffrn_orient_matrix_UB_13      0.0371076000
_diffrn_orient_matrix_UB_21      0.0144824000
_diffrn_orient_matrix_UB_22      -0.0290524000
_diffrn_orient_matrix_UB_23      -0.0232094000
_diffrn_orient_matrix_UB_31      0.0518301000
_diffrn_orient_matrix_UB_32      0.0018361000
_diffrn_orient_matrix_UB_33      0.0028071000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            38329
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         1.985
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       block
_exptl_crystal_F_000             1299
_exptl_crystal_size_max          0.2634
_exptl_crystal_size_mid          0.1158
_exptl_crystal_size_min          0.0771
_refine_diff_density_max         0.841
_refine_diff_density_min         -0.791
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     819
_refine_ls_number_reflns         12279
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1252
_refine_ls_R_factor_gt           0.0829
_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^)+(0.1275P)^2^+3.1560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2304
_refine_ls_wR_factor_ref         0.2623
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7774
_reflns_number_total             12279
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc03289c2.cif
_cod_data_source_block           2
_cod_original_formula_sum        'C125 H227 N10 O31.50'
_cod_database_code               7124663
_chemical_oxdiff_formula         'C20 H20 O8 N2'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H8S of O8S, All C(H,H) groups, All N(H,H) groups, All N(H,
  H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H27 of O27, H25 of O25, H11 of O11, H9S of O9S, H7S of
  O7S, H6S of O6S, H6 of O6, H5S of O5S, H4S of O4S, H4 of O4, H3S of O3S, H2S
  of O2S, H1S of O1S, All O(H,H) groups
2. Restrained distances
 C3S-O3S
 1.45 with sigma of 0.02
 C2S-O2S
 1.45 with sigma of 0.02
 O6S-C6S
 1.45 with sigma of 0.02
 O7S-C7S
 1.45 with sigma of 0.01
 O3S-C3S
 1.45 with sigma of 0.02
 O2S-C2S
 1.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C2S) \\sim Ueq, Uanis(O8S) \\sim Ueq, Uanis(C6S) \\sim Ueq, Uanis(C7S)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O7S) \\sim Ueq, Uanis(O1W) \\sim Ueq, Uanis(C3S) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.01
Uanis(O2S) = Uanis(O3S)
Uanis(C2S) = Uanis(C3S)
4. Others
 Fixed Sof: O1W(0.25) H1WA(0.25) H1WB(0.25) O2S(0.5) H2S(0.5) O3S(0.5)
 H3S(0.5) H6(0.5) O7S(0.5) H7S(0.5) H25(0.5) C2S(0.5) H2SA(0.5) H2SB(0.5)
 H2SC(0.5) C3S(0.5) H3SA(0.5) H3SB(0.5) H3SC(0.5) C7S(0.5) H7SA(0.5) H7SB(0.5)
 H7SC(0.5) C8S(0.25) H8SA(0.25) H8SB(0.25) H8SC(0.25) C8SA(0.75) H8SD(0.75)
 H8SE(0.75) H8SF(0.75)
5.a Riding coordinates:
 O1W(H1WA,H1WB), O3S(H3S), O7S(H7S), O8S(H8S), O9S(H9S)
5.b Ternary CH refined with riding coordinates:
 C1A(H1A), C1B(H1B), C1C(H1C), C2A(H2A), C2B(H2B), C7(H7), C14(H14), C21(H21),
 C28(H28)
5.c Secondary CH2 refined with riding coordinates:
 C2C(H2CA,H2CB), C3A(H3AA,H3AB), C3B(H3BA,H3BB), C3C(H3CA,H3CB), C4A(H4AA,
 H4AB), C4B(H4BA,H4BB), C5A(H5AA,H5AB), C5B(H5BA,H5BB), C6A(H6AA,H6AB),
 C6B(H6BA,H6BB), C29(H29A,H29B), C31(H31A,H31B), C33(H33A,H33B), C35(H35A,H35B)
5.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C16(H16), C23(H23)
5.e Idealised Me refined as rotating group:
 N1A(H1AA,H1AB,H1AC), N1C(H1CA,H1CB,H1CC), N2A(H2AA,H2AB,H2AC), N2B(H2BA,H2BB,
 H2BC), C1S(H1SA,H1SB,H1SC), C2S(H2SA,H2SB,H2SC), C3S(H3SA,H3SB,H3SC), C4S(H4SA,
 H4SB,H4SC), C5S(H5SA,H5SB,H5SC), C6S(H6SA,H6SB,H6SC), C7S(H7SA,H7SB,H7SC),
 C8S(H8SA,H8SB,H8SC), C8SA(H8SD,H8SE,H8SF), C9S(H9SA,H9SB,H9SC), C30(H30A,H30B,
 H30C), C32(H32A,H32B,H32C), C34(H34A,H34B,H34C), C36(H36A,H36B,H36C), C37(H37A,
 H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C)
5.f Idealised tetrahedral OH refined as rotating group:
 O1S(H1S), O2S(H2S), O4(H4), O4S(H4S), O5S(H5S), O6(H6), O6S(H6S), O11(H11),
 O25(H25), O27(H27)
;
_shelx_res_checksum              6467
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'