Chiral crystals from porphyrinoids possessing a very low racemization barrier
Śniechowska, Justyna; Paluch, Piotr; Bujacz, Grzegorz; Górecki, Marcin; Frelek, Jadwiga; Gryko, Daniel T.; Potrzebowski, Marek J.; CrystEngComm 18 (2016) 3561–; doi:10.1039/C6CE00530F

data_7224951
_publ_section_title
;
 Chiral crystals from porphyrinoids possessing a very low racemization
 barrier
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              3561
_journal_paper_doi               10.1039/C6CE00530F
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C37 H11 F15 N4, 2(C H2 Cl2)'
_chemical_formula_sum            'C39 H15 Cl4 F15 N4'
_chemical_formula_weight         966.37
_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_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_date             2015-11-26
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)

Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H.
 (2013). in preparation.

Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H.
 (2015). Acta Cryst. A71, 59-75.

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.
;
_audit_update_record
;
2015-11-26 deposited with the CCDC.
2016-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.412(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5184(9)
_cell_length_b                   13.4639(8)
_cell_length_c                   21.0031(13)
_cell_measurement_reflns_used    2802
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      67.9951
_cell_measurement_theta_min      2.1911
_cell_volume                     3667.0(4)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector_area_resol_mean 8.1956
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_details
;
  1 omega  -90.00  -37.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  179.0000 -150.0000 53

  2 omega  -21.00   50.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -104.0000 -168.0000 71

  3 omega  -70.00  -41.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  179.0000  -30.0000 29

  4 omega  -79.00  -38.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  179.0000  -60.0000 41

  5 omega  -80.00  -33.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  179.0000   30.0000 47

  6 omega -155.00  -18.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -59.5000  -77.0000  -90.0000 137

  7 omega  125.00  152.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       59.5000  125.0000   30.0000 27

  8 omega  -22.00    4.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       59.5000  -77.0000  -60.0000 26

  9 omega   77.00  144.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       59.5000  125.0000 -150.0000 67

 10 omega   38.00   89.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       59.5000  -77.0000  -60.0000 51

 11 omega  -66.00  -35.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -93.0000   25.0000  -60.0000 31

 12 omega  -66.00  -18.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -93.0000   25.0000 -180.0000 48

 13 omega   39.00  145.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000  179.0000    0.0000 106

 14 omega  125.00  160.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000  -25.0000   30.0000 35

 15 omega  143.00  171.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000  111.0000   90.0000 28

 16 omega   99.00  125.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000  111.0000   90.0000 26

 17 omega  148.00  174.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000  111.0000  -30.0000 26

 18 omega   55.00   81.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000  -50.0000    0.0000 26

 19 omega   80.00  107.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000  111.0000  -30.0000 27

 20 omega  109.00  136.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000  179.0000   30.0000 27

 21 omega   44.00   92.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000  179.0000   30.0000 48

 22 omega   38.00   63.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000  -50.0000  150.0000 25

 23 omega  124.00  156.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000  -25.0000  150.0000 32

 24 omega   41.00   91.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000 -104.0000   11.0000 50

 25 omega   29.00   61.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000  -50.0000  -90.0000 32

 26 omega  146.00  177.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000  -25.0000 -150.0000 31

 27 omega  124.00  169.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000  -25.0000 -180.0000 45

 28 omega   98.00  158.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000  -90.0000 -128.0000 60

 29 omega   21.00   46.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      119.0000  -90.0000 -128.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0835313000
_diffrn_orient_matrix_UB_12      -0.0515647000
_diffrn_orient_matrix_UB_13      0.0555247000
_diffrn_orient_matrix_UB_21      0.0617016000
_diffrn_orient_matrix_UB_22      0.0977271000
_diffrn_orient_matrix_UB_23      0.0139014000
_diffrn_orient_matrix_UB_31      -0.0577112000
_diffrn_orient_matrix_UB_32      0.0295627000
_diffrn_orient_matrix_UB_33      0.0507355000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_unetI/netI     0.1531
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18029
_diffrn_reflns_theta_full        25.3240
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_min         1.57
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.7503
_exptl_crystal_description       prism
_exptl_crystal_F_000             1923.8564
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.6357
_refine_diff_density_min         -1.4112
_refine_diff_density_rms         0.1939
_refine_ls_d_res_high            0.8308
_refine_ls_d_res_low             12.9676
_refine_ls_goodness_of_fit_ref   0.8832
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     603
_refine_ls_number_reflns         6687
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      0.8776
_refine_ls_R_factor_all          0.1398
_refine_ls_R_factor_gt           0.0682
_refine_ls_shift/su_max          0.0813
_refine_ls_shift/su_mean         0.0175
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0918P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1915
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -16
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                3114
_reflns_number_total             6687
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6ce00530f2.cif
_cod_data_source_block           korol_P21c
_cod_depositor_comments
'Adding full bibliography for 7224951--7224952.cif.'
_cod_database_code               7224951
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C38-Cl1 = C38-Cl2 = C38"-Cl1" = C38"-Cl2"
 1.77 with sigma of 0.001
 Cl1-Cl2 = Cl1"-Cl2"
 2.93 with sigma of 0.001
 C39-Cl3 = C39-Cl4 = C39'-Cl3 = C39'-Cl4'
 1.77 with sigma of 0.001
 Cl3-Cl4 = Cl3-Cl4'
 2.93 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
C38" \\sim Cl1" \\sim Cl2": within 1.8A with sigma of 0.01 and sigma for
terminal atoms of 0.02
C39' \\sim Cl4': within 1.8A with sigma of 0.01 and sigma for terminal atoms of
0.02
Uanis(C38) \\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(Cl2) \\sim Ueq: with sigma of
0.05 and sigma for terminal atoms of 0.1
Uanis(C38") \\sim Ueq, Uanis(Cl1") \\sim Ueq, Uanis(Cl2") \\sim Ueq: with sigma
of 0.05 and sigma for terminal atoms of 0.1
Uanis(C39') \\sim Ueq, Uanis(Cl4') \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.1
4. Others
 Fixed Sof: H1(0.75) H2(0.25) C38(0.92) H38a(0.92) H38b(0.92) Cl1(0.92)
 Cl2(0.92) C38"(0.08) H38c(0.08) H38d(0.08) Cl1"(0.08) Cl2"(0.08) C39(0.97)
 H39a(0.97) H39b(0.97) Cl4(0.97) C39'(0.03) H39c(0.03) H39d(0.03) Cl4'(0.03)
5.a Secondary CH2 refined with riding coordinates:
 C38(H38a,H38b), C38"(H38c,H38d), C39(H39a,H39b), C39'(H39c,H39d)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N4(H4), C2(H2a), C3(H3a), C7(H7), C8(H8), C12(H12),
 C13(H13), C17(H17), C18(H18)
;
_olex2_submission_special_instructions 'No special instructions were received'