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_7228486
_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, 3(C6 H7 N O)'
_chemical_formula_sum            'C54 H57 Br4 N3 O11'
_chemical_formula_weight         1243.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-07
_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                 91.720(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8438(4)
_cell_length_b                   26.2609(6)
_cell_length_c                   14.0294(3)
_cell_measurement_reflns_used    7793
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      74.0530
_cell_measurement_theta_min      4.5310
_cell_volume                     5098.1(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      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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   -115.00  -5.00   1.00   10.00    --  -41.90 -19.00   0.00  110
  2  \w     23.00  98.00   1.00   10.00    --   41.90-125.00 -90.00   75
  3  \w     78.00 178.00   1.00   40.00    --  106.66  61.00 -60.00  100
  4  \w    100.00 178.00   1.00   40.00    --  106.66 125.00-150.00   78
  5  \w     48.00 139.00   1.00   40.00    --  106.66 -77.00 150.00   91
  6  \w     94.00 178.00   1.00   40.00    --  106.66 125.00 120.00   84
;
_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      -0.0826890000
_diffrn_orient_matrix_UB_12      -0.0079415000
_diffrn_orient_matrix_UB_13      0.0697164000
_diffrn_orient_matrix_UB_21      -0.0307095000
_diffrn_orient_matrix_UB_22      0.0559388000
_diffrn_orient_matrix_UB_23      -0.0134708000
_diffrn_orient_matrix_UB_31      -0.0680432000
_diffrn_orient_matrix_UB_32      -0.0156117000
_diffrn_orient_matrix_UB_33      -0.0838481000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17258
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        66.737
_diffrn_reflns_theta_max         66.737
_diffrn_reflns_theta_min         3.573
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.390
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_description       plate
_exptl_crystal_F_000             2520
_exptl_crystal_size_max          0.092
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.024
_refine_diff_density_max         3.745
_refine_diff_density_min         -1.002
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     658
_refine_ls_number_reflns         8948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0757
_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^)+(0.0798P)^2^+65.1622P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2028
_refine_ls_wR_factor_ref         0.2078
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7747
_reflns_number_total             8948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00975e2.cif
_cod_data_source_block           4_BrC2
_cod_database_code               7228486
_chemical_oxdiff_formula         'C20 H20 N1 O9 Br4'
_reflns_odcompleteness_completeness 98.66
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O18(H18), O27(H27), O20(H20), O6(H6), O11(H11), O13(H13)
2.b Ternary CH refined with riding coordinates:
 C28(H28), C21(H21), C14(H14), C7(H7)
2.c Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C35(H35A,H35B), C33(H33A,H33B), C31(H31A,H31B)
2.d Aromatic/amide H refined with riding coordinates:
 C16(H16), C2(H2), C23(H23), C9(H9), C47(H47), C46(H46), C43(H43), C49(H49),
 C53(H53), C44(H44), C37(H37), C50(H50), C42(H42), C52(H52), C38(H38), C41(H41)
2.e Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C36(H36A,H36B,H36C), C30(H30A,H30B,H30C), C34(H34A,H34B,
 H34C), C40(H40A,H40B,H40C), C48(H48A,H48B,H48C), C54(H54A,H54B,H54C)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O25(H25)
;
_shelx_res_checksum              63564
_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 1.104
_oxdiff_exptl_absorpt_empirical_full_min 0.912