Greener solid-state synthesis: stereo-selective [2 + 2] photodimerization of vitamin K3controlled by halogen bonding
Zhu, Bingqing; Wang, Jian-Rong; Zhang, Qi; Mei, Xuefeng; CrystEngComm 18 (2016) 6327–; doi:10.1039/C6CE01236A

data_7225840
_publ_section_title
;
 Greener solid-state synthesis: stereo-selective [2 + 2] photodimerization
 of vitamin K3controlled by halogen bonding
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              6327
_journal_paper_doi               10.1039/C6CE01236A
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C6 F4 I2, C11 H8 O2'
_chemical_formula_sum            'C17 H8 F4 I2 O2'
_chemical_formula_weight         574.03
_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   geom
_audit_creation_date             2016-03-03
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-03-29 deposited with the CCDC.
2016-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.088(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0631(12)
_cell_length_b                   4.1837(3)
_cell_length_c                   24.5252(19)
_cell_measurement_reflns_used    4888
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      2.61
_cell_volume                     1723.7(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15020
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.578
_diffrn_reflns_theta_min         1.593
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.697
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0735 before and 0.0426 after correction.
The Ratio of minimum to maximum transmission is 0.7082.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.704
_refine_diff_density_min         -0.956
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0308P)^2^+3.7047P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0795
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3001
_reflns_number_total             3937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce01236a2.cif
_cod_data_source_block           2015620
_cod_depositor_comments
'Adding full bibliography for 7225839--7225840.cif.'
_cod_database_code               7225840
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C3(H3), C7(H7), C8(H8)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              62482
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'