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_7228482
_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, 0.5(C16 H22 N2 O2), H2 O, 2(C3 H6 O)'
_chemical_formula_sum            'C50 H61 Br4 N O12'
_chemical_formula_weight         1187.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 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                 104.628(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.3678(8)
_cell_length_b                   7.9991(3)
_cell_length_c                   22.9088(11)
_cell_measurement_reflns_used    3314
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.2360
_cell_measurement_theta_min      3.6070
_cell_volume                     2724.9(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      air
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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    -94.00 -35.00   1.00   30.00    --  -18.14-178.00 -60.00   59
  2  \w      4.00  55.00   1.00   30.00    --   19.23  57.00 120.00   51
  3  \w      3.00  91.00   1.00   30.00    --   19.23  37.00-120.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0239675000
_diffrn_orient_matrix_UB_12      0.0759945000
_diffrn_orient_matrix_UB_13      -0.0078118000
_diffrn_orient_matrix_UB_21      -0.0240704000
_diffrn_orient_matrix_UB_22      -0.0157713000
_diffrn_orient_matrix_UB_23      0.0220638000
_diffrn_orient_matrix_UB_31      0.0334688000
_diffrn_orient_matrix_UB_32      0.0429231000
_diffrn_orient_matrix_UB_33      0.0218370000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11117
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         3.137
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.011
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84080
_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            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       plate
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.036
_refine_diff_density_max         1.525
_refine_diff_density_min         -1.223
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4906
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0832P)^2^+5.5762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1434
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4052
_reflns_number_total             4906
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00975e2.cif
_cod_data_source_block           acetone_BrC2_6
_cod_original_cell_volume        2724.8(2)
_cod_database_code               7228482
_chemical_oxdiff_formula         'C30 H30 N1 O9 Br4'
_reflns_odcompleteness_completeness 98.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. 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, All O(H,H) groups
2. Restrained distances
 C31-C29
 2.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C26) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C31) = Uanis(C30) = Uanis(O30) = Uanis(C29)
Uanis(C21) = Uanis(C26)
4. Others
 Fixed Sof: O1(0.5) O1W(0.5) H1WA(0.5) H1WB(0.5) O30(0.5) C22(0.5) H22(0.5)
 C21(0.5) C20(0.5) H20(0.5) C19(0.5) N1(0.5) C23(0.5) C24(0.5) H24A(0.5)
 H24B(0.5) H24C(0.5) C25(0.5) H25A(0.5) H25B(0.5) H25C(0.5) C26(0.5) H26A(0.5)
 H26B(0.5) H26C(0.5) C29(0.5) H29A(0.5) H29B(0.5) H29C(0.5) C30(0.5) C31(0.5)
 H31A(0.5) H31B(0.5) H31C(0.5)
5.a Riding coordinates:
 O1W(H1WA,H1WB), O11(H11), O13(H13)
5.b Ternary CH refined with riding coordinates:
 C7(H7), C14(H14)
5.c Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B)
5.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C22(H22), C20(H20)
5.e Fitted hexagon refined as free rotating group:
 C22(C21,C20,C19,N1,C23)
5.f Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C31(H31A,
 H31B,H31C)
5.g Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6)
;
_shelx_res_checksum              97303
_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 1.157
_oxdiff_exptl_absorpt_empirical_full_min 0.878