Endo-/Exo- and Halogen Bonded Complexes of Conformationally Rigid Cethyl-2-bromoresorcinarene and aromatic N-oxides
Puttreddy, Rakesh; Beyeh, Ngong Kodiah; Ras, Robin H.A.; Trant, John; Rissanen, Kari; CrystEngComm  (2017) –; doi:10.1039/C7CE00975E

data_7228484
_publ_section_title
;
 Endo-/Exo- and Halogen Bonded Complexes of Conformationally Rigid
 Cethyl-2-bromoresorcinarene and aromatic N-oxides
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00975E
_journal_year                    2017
_chemical_formula_moiety         'C36 H36 Br4 O8, 2(C9 H7 N O), 2(C3 H6 O)'
_chemical_formula_sum            'C60 H62 Br4 N2 O12'
_chemical_formula_weight         1322.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2017-05-22 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.897(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.3967(6)
_cell_length_b                   7.78520(18)
_cell_length_c                   27.8052(8)
_cell_measurement_reflns_used    4884
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.9580
_cell_measurement_theta_min      4.4450
_cell_volume                     5457.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -66.00  33.00   1.00    6.00    --  -41.90  37.00 120.00   99
  2  \w      1.00  83.00   1.00    6.00    --   41.90 -99.00-120.00   82
  3  \w     77.00 153.00   1.00   24.00    --  106.66  77.00 -60.00   76
  4  \w     24.00 103.00   1.00   24.00    --  106.66 -94.00  60.00   79
  5  \w     36.00 117.00   1.00   24.00    --  106.66-125.00 -90.00   81
  6  \w     37.00 134.00   1.00   24.00    --  106.66 -61.00-120.00   97
  7  \w     92.00 144.00   1.00   24.00    --  106.66  61.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0285643000
_diffrn_orient_matrix_UB_12      -0.0856828000
_diffrn_orient_matrix_UB_13      0.0459380000
_diffrn_orient_matrix_UB_21      0.0078944000
_diffrn_orient_matrix_UB_22      0.1771019000
_diffrn_orient_matrix_UB_23      0.0244003000
_diffrn_orient_matrix_UB_31      -0.0534428000
_diffrn_orient_matrix_UB_32      -0.0194956000
_diffrn_orient_matrix_UB_33      0.0203794000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9196
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        66.730
_diffrn_reflns_theta_max         66.730
_diffrn_reflns_theta_min         3.675
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.150
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92465
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.610
_exptl_crystal_description       needle
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.107
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.022
_refine_diff_density_max         3.507
_refine_diff_density_min         -0.848
_refine_diff_density_rms         0.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         4865
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0549
_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^)+(0.0451P)^2^+140.8365P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1626
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4424
_reflns_number_total             4865
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00975e2.cif
_cod_data_source_block           acetone_BrC2_8
_cod_database_code               7228484
_chemical_oxdiff_formula         'C20 H20 O9 N1 Br2'
_reflns_odcompleteness_completeness 98.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9363(11) 0.0637(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 C30-C31
 1.54 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C32) \\sim Ueq, Uanis(C30) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C13) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: O6(0.5) C30(0.5) H30A(0.5) H30B(0.5) H30C(0.5) C31(0.5) C32(0.5)
 H32A(0.5) H32B(0.5) H32C(0.5)
6.a Riding coordinates:
 O1(H1), O2(H2), O3(H3)
6.b Ternary CH refined with riding coordinates:
 C7(H7), C16(H16)
6.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C17(H17A,H17B)
6.d Aromatic/amide H refined with riding coordinates:
 C2(H2A), C9(H9), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26),
 C27(H27)
6.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C32(H32A,H32B,H32C)
6.f Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              57090
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.128
_oxdiff_exptl_absorpt_empirical_full_min 0.882