Halogen bonding influences perylene-core twists in non-core substituted perylene tetraesters
Wojciechowski, Jonathan P.; Martin, Adam D.; Bhadbhade, Mohan; Webb, James E. A.; Thordarson, Pall; CrystEngComm 18 (2016) 4513–; doi:10.1039/C6CE00929H

data_7225243
_publ_section_title
;
 Halogen bonding influences perylene-core twists in non-core substituted
 perylene tetraesters
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              4513
_journal_paper_doi               10.1039/C6CE00929H
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         '2(C H Br3), C32 H28 O8'
_chemical_formula_sum            'C34 H30 Br6 O8'
_chemical_formula_weight         1046.04
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-10-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-03-14 deposited with the CCDC.
2016-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3120(15)
_cell_length_b                   23.629(5)
_cell_length_c                   20.889(4)
_cell_measurement_temperature    100
_cell_volume                     3609.1(13)
_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      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Australian Synchrotron'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0892
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            69506
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.085
_diffrn_reflns_theta_min         1.301
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.724
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.925
_exptl_crystal_description       plate
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.015
_refine_diff_density_max         1.196
_refine_diff_density_min         -1.199
_refine_diff_density_rms         0.144
_refine_ls_abs_structure_details
;
 Flack x determined using 4873 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.487(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         10581
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0498
_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^)+(0.0826P)^2^+10.6738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1310
_reflns_Friedel_coverage         0.948
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                10341
_reflns_number_total             10581
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce00929h2.cif
_cod_data_source_block           jono_4_a
_cod_depositor_comments
'Adding full bibliography for 7225240--7225243.cif.'
_cod_database_code               7225243
_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
2.a Ternary CH refined with riding coordinates:
 C1A(H1A), C1B(H1B)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C25(H25A,H25B), C28(H28A,H28B), C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C26(H26A,H26B,H26C), C29(H29A,H29B,H29C), C32(H32A,H32B,
 H32C)
;
_shelx_res_checksum              82280
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'