Taco complex-templated highly regio- and stereo-selective photodimerization of a coumarin-containing crown ether
Wei, Peifa; Wang, Haoze; Jie, Kecheng; Huang, Feihe; Chemical Communications (Cambridge, United Kingdom) 53 (2017) 1688–1691; doi:10.1039/c6cc10089a

data_7119588
_publ_section_title
;
 Taco complex-templated highly regio- and stereo-selective
 photodimerization of a coumarin-containing crown ether
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   10
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              1688
_journal_page_last               1691
_journal_paper_doi               10.1039/c6cc10089a
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety
'2(C50 H55 O16), 2(C14 H12 N2), 4(F6 P), 10(C2 H3 N), H2 O'
_chemical_formula_sum            'C148 H166 F24 N14 O33 P4'
_chemical_formula_weight         3248.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2016-09-27 deposited with the CCDC.
2017-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.925(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   26.2806(15)
_cell_length_b                   10.5229(5)
_cell_length_c                   28.8376(16)
_cell_measurement_reflns_used    5744
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.5063
_cell_measurement_theta_min      3.1031
_cell_volume                     7705.9(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0015625000
_diffrn_orient_matrix_UB_12      0.0467954000
_diffrn_orient_matrix_UB_13      0.0180525000
_diffrn_orient_matrix_UB_21      0.0256393000
_diffrn_orient_matrix_UB_22      -0.0213987000
_diffrn_orient_matrix_UB_23      0.0118371000
_diffrn_orient_matrix_UB_31      0.0109507000
_diffrn_orient_matrix_UB_32      0.0435322000
_diffrn_orient_matrix_UB_33      -0.0135165000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            29849
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.11
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3384
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.755
_refine_diff_density_min         -1.134
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1019
_refine_ls_number_reflns         14066
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0799
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1119P)^2^+9.8601P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2039
_refine_ls_wR_factor_ref         0.2361
_reflns_number_gt                9205
_reflns_number_total             14066
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7119524
_cod_data_source_file            c6cc10089a2.cif
_cod_data_source_block           160605_pfw_196_g6_a
_cod_database_code               7119588
_chemical_oxdiff_formula         'c10 h10 n2 o8 p1 f6'
_reflns_odcompleteness_completeness 99.60
_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,H) groups
2. Uiso/Uaniso restraints and constraints
C73 \\sim C72 \\sim C71 \\sim N6 \\sim C70 \\sim C68 \\sim N7 \\sim C73: within
1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: O17(0.5) H17A(0.5) H17B(0.5)
4.a Free rotating group:
 O17(H17A,H17B)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B),
 C13(H13A,H13B), C14(H14A,H14B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B),
  C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,
 H28B), C29(H29A,H29B), C40(H40A,H40B), C63(H63A,H63B), C64(H64A,H64B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C11(H11), C16(H16), C18(H18), C20(H20), C31(H31),
 C32(H32), C35(H35), C37(H37), C42(H42), C43(H43), C46(H46), C48(H48), C51(H51),
  C52(H52), C53(H53), C58(H58), C59(H59), C60(H60), C61(H61), C62(H62)
4.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C50(H50A,H50B,H50C), C68(H68A,H68B,H68C), C70(H70A,H70B,
 H70C), C72(H72A,H72B,H72C), C66(H66A,H66B,H66C), C74(H74A,H74B,H74C)
;