Synthesis and Photophysical Properties of Chalcophenes-Embedded Cycloparaphenylenes.
Zhao, Hongyan; Ma, Ying-Chao; Cao, Lei; Huang, Shiqing; Zhang, Jian-Ping; Yan, Xiaoyu; The Journal of organic chemistry 84 (2019) 5230–5235; doi:10.1021/acs.joc.9b00207

data_4034299
_publ_section_title
;
 Synthesis and Photophysical Properties of Chalcophenes-Embedded
 Cycloparaphenylenes.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5230
_journal_page_last               5235
_journal_paper_doi               10.1021/acs.joc.9b00207
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C64 H40 Se4, 2(C H2 Cl2)'
_chemical_formula_sum            'C66 H44 Cl4 Se4'
_chemical_formula_weight         1294.65
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-31 deposited with the CCDC.
2019-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                79.176(4)
_cell_angle_beta                 80.799(4)
_cell_angle_gamma                74.552(4)
_cell_formula_units_Z            2
_cell_length_a                   9.9408(11)
_cell_length_b                   17.8727(18)
_cell_length_c                   19.770(2)
_cell_measurement_reflns_used    7266
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      24.619
_cell_measurement_theta_min      2.229
_cell_volume                     3302.9(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      180.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2307
_diffrn_reflns_av_unetI/netI     0.1998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            47316
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         2.229
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.418
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       needle
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.178
_refine_diff_density_min         -1.112
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         15149
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1592
_refine_ls_R_factor_gt           0.0863
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2037
_refine_ls_wR_factor_ref         0.2348
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7951
_reflns_number_total             15149
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00207_si_002.cif
_cod_data_source_block           mo_zhy2018090201_0m_sqd
_cod_database_code               4034299
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.777
_shelx_estimated_absorpt_t_min   0.618
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C1-Cl1 \\sim C1-Cl2
 with sigma of 0.02
3. Rigid bond restraints
 C1, Cl1, Cl2
 with sigma for 1-2 distances of 0.05 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
C1 \\sim Cl1 \\sim Cl2: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04
5. Same fragment restrains
{C1, Cl1, Cl2} sigma for 1-2: 0.02, 1-3: 0.04
as
{C2, Cl3, Cl4}
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
6.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00C(H00C), C00G(H00G), C00H(H00H), C00O(H00O),
 C00P(H00P), C00S(H00S), C00T(H00T), C00U(H00U), C00W(H00W), C010(H010),
 C012(H012), C013(H013), C014(H014), C015(H015), C017(H017), C01A(H01A),
 C01B(H01B), C01C(H01C), C01D(H01D), C01E(H01E), C01F(H01F), C01G(H01G),
 C01I(H01I), C01J(H01J), C01K(H01K), C01L(H01L), C01M(H01M), C01P(H01P),
 C01Q(H01Q), C01R(H01R), C01T(H01T), C01U(H01U), C01V(H01V), C01W(H01W),
 C01X(H01X), C01Y(H01Y), C01Z(H01Z), C021(H021)
;
_shelx_res_checksum              93093
_shelx_hkl_checksum              46813
_olex2_submission_special_instructions 'No special instructions were received'
_platon_squeeze_void_probe_radius 1.20