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_7225242
_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         'C32 H28 O8, C2 Cl2'
_chemical_formula_sum            'C34 H28 Cl2 O8'
_chemical_formula_weight         635.46
_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   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                 101.83(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.689(5)
_cell_length_b                   15.869(3)
_cell_length_c                   7.1690(14)
_cell_measurement_temperature    100
_cell_volume                     2971.8(10)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_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  0.1190
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            28750
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.258
_diffrn_reflns_theta_min         1.559
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       plate
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.361
_refine_diff_density_min         -1.014
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.768
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         4368
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.842
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0884
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2488
_refine_ls_wR_factor_ref         0.2597
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3590
_reflns_number_total             4368
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce00929h2.cif
_cod_data_source_block           jono_3
_cod_depositor_comments
'Adding full bibliography for 7225240--7225243.cif.'
_cod_original_cell_volume        2971.7(11)
_cod_database_code               7225242
_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. Restrained distances
 Cl1_$2-C4AA
 2.68 with sigma of 0.02
 Cl1-C4AA
 1.78 with sigma of 0.02
 C4AA_$1-C1_$1
 1.5 with sigma of 0.02
 Cl0A_$2-C4AA = Cl1-C1_$3 = Cl1_$3-C4AA_$3
 1.78 with sigma of 0.02
 C4AA-Cl0A
 2.68 with sigma of 0.02
 Cl1-C4AA_$3
 2.68 with sigma of 0.02
 C1_$1-Cl1_$1
 2.68 with sigma of 0.02
 C6AA-C1_$3 \\sim C6AA-C4AA \\sim C4AA-C1
 with sigma of 0.02
3. Rigid bond restraints
 Cl1, C4AA, Cl1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Others
 Fixed Sof: Cl1(0.5) C4AA(0.5) Cl0A(0.5) C1(0.25) C6AA(0.25)
5.a Secondary CH2 refined with riding coordinates:
 C5AA(H5AA,H5AB), C15(H15A,H15B)
5.b Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), C3AA(H3AA), C5(H5), C2AA(H2AA)
5.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              32674
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'