Schiff-base [4]helicene Zn(II) complexes as chiral emitters.
Savchuk, Mariia; Vertueux, Steven; Cauchy, Thomas; Loumaigne, Matthieu; Zinna, Francesco; Di Bari, Lorenzo; Zigon, Nicolas; Avarvari, Narcis; Dalton transactions (Cambridge, England : 2003) 50 (2021) 10533–10539; doi:10.1039/d1dt01752g

data_7707784
_publ_section_title
;
 Schiff-base [4]helicene Zn(II) complexes as chiral emitters.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10533
_journal_page_last               10539
_journal_paper_doi               10.1039/d1dt01752g
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C44 H34 N2 O3 Zn'
_chemical_formula_sum            'C44 H34 N2 O3 Zn'
_chemical_formula_weight         704.10
_chemical_name_systematic
'Zn salen cyclohexyldiamine (R,R) [4]helicene'
_space_group_crystal_system      monoclinic
_space_group_IT_number           3
_space_group_name_Hall           'P 2y'
_space_group_name_H-M_alt        'P 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-04-27
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-04-29 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.642(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.960(3)
_cell_length_b                   8.349(2)
_cell_length_c                   20.342(4)
_cell_measurement_reflns_used    560
_cell_measurement_temperature    150(10)
_cell_measurement_theta_max      30.0110
_cell_measurement_theta_min      3.1220
_cell_volume                     3389.7(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -40.00  33.00   1.00   34.97    --    0.00 -77.00-120.00   73
  2  \w    -33.00  42.00   1.00   34.97    --    0.00  77.00  90.00   75
  3  \w      9.00  71.00   1.00   42.34    --   81.13 -61.00 120.00   62
  4  \w     -2.00 107.00   1.00   42.34    --   81.13 -94.00-150.00  109
  5  \w      8.00  51.00   1.00   42.34    --   81.13 -45.00 -30.00   43
  6  \w     19.00  61.00   1.00   42.34    --   81.13 -61.00-120.00   42
  7  \w      5.00  35.00   1.00   42.34    --   81.13 -30.00-180.00   30
  8  \w     36.00 112.00   1.00   42.34    --   81.13-125.00 120.00   76
  9  \w      9.00  47.00   1.00   42.34    --   81.13 -61.00  30.00   38
 10  \w      5.00  30.00   1.00   42.34    --   81.13 -30.00-150.00   25
 11  \w     14.00 105.00   1.00   42.34    --   81.13 -77.00 -60.00   91
 12  \w      3.00 154.00   1.00   42.34    --   81.13   0.00-150.00  151
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0047557000
_diffrn_orient_matrix_UB_12      -0.1404370000
_diffrn_orient_matrix_UB_13      -0.0488925000
_diffrn_orient_matrix_UB_21      -0.0043935000
_diffrn_orient_matrix_UB_22      -0.1194772000
_diffrn_orient_matrix_UB_23      0.0574176000
_diffrn_orient_matrix_UB_31      -0.0769493000
_diffrn_orient_matrix_UB_32      -0.0020172000
_diffrn_orient_matrix_UB_33      -0.0072078000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1775
_diffrn_reflns_av_unetI/netI     0.2632
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13248
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        50.419
_diffrn_reflns_theta_max         50.419
_diffrn_reflns_theta_min         3.085
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.360
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019) 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    1.380
_exptl_crystal_description       needle
_exptl_crystal_F_000             1464
_exptl_crystal_preparation       'vapor diffusion of MeOH in THF'
_exptl_crystal_recrystallization_method 'vapor diffusion of MeOh in THF'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 405 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_extinction_coef       0.00051(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     868
_refine_ls_number_reflns         7046
_refine_ls_number_restraints     698
_refine_ls_restrained_S_all      1.236
_refine_ls_R_factor_all          0.2592
_refine_ls_R_factor_gt           0.0853
_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^)+(0.0455P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.2361
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                1981
_reflns_number_total             7046
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt01752g2.cif
_cod_data_source_block           exp_1368_a
_cod_depositor_comments
;
Adding full bibliography for 7707781--7707784.cif.

2024-09-23
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C88 H68 N4 O6 Zn2'
_cod_original_formula_weight         1408.20
_cod_original_formula_moiety         '2(C44 H34 N2 O3 Zn)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        3389.7(13)
_cod_database_code               7707784
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C44H32O2N2Zn
_chemical_oxdiff_usercomment     'yellow needle'
_cell_oxdiff_angle_alpha         90.085(15)
_cell_oxdiff_angle_beta          90.684(11)
_cell_oxdiff_angle_gamma         90.048(11)
_cell_oxdiff_length_a            19.951(2)
_cell_oxdiff_length_b            8.3547(15)
_cell_oxdiff_length_c            20.337(4)
_cell_oxdiff_measurement_reflns_used 560
_cell_oxdiff_volume              3389.7(9)
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.935
_diffrn_oxdiff_digest_frames
;
0103aec69cfca905f3ea9999b45fbecd7700027a2ae
;
_diffrn_oxdiff_digest_hkl
;
015e24549f2222fd21821f33afdadba950d11e
;
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H6A,H6B} of O6, All C(H,H) groups
 At 1.5 times of:
  {H3A,H3B} of O3
2. Restrained distances
 O6-H6B = O6-H6A
 0.84 with sigma of 0.005
 O3-H3A = O3-H3B
 0.84 with sigma of 0.005
 H6B-H6A
 1.33 with sigma of 0.005
 H3A-H3B
 1.33 with sigma of 0.01
 Zn2-H6B \\sim Zn2-H6A
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
C45 \\sim C47 \\sim C48 \\sim C51 \\sim C50 \\sim C49 \\sim C53 \\sim C52 \\sim
C54 \\sim C55 \\sim C58 \\sim C57 \\sim C56 \\sim C59 \\sim C61 \\sim C60 \\sim
C62 \\sim C63 \\sim C65 \\sim C64 \\sim C66 \\sim C69 \\sim C68 \\sim C67 \\sim
C70 \\sim C71 \\sim C73 \\sim C74 \\sim C75 \\sim C76 \\sim C72 \\sim C46 \\sim
C77 \\sim C78 \\sim C80 \\sim C79 \\sim C81 \\sim C82 \\sim C83 \\sim C84 \\sim
C88 \\sim C87 \\sim C86 \\sim C85 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5
\\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13
\\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21
\\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27 \\sim C29 \\sim C30
\\sim C31 \\sim C32 \\sim C28 \\sim C33 \\sim C34 \\sim C35 \\sim C36 \\sim C37
\\sim C38 \\sim C39 \\sim C40 \\sim C41 \\sim C42 \\sim C43 \\sim C44 \\sim N4
\\sim N2 \\sim N1 \\sim N3: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Uanis(C1) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C6) \\sim
Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
4. Rigid body (RIGU) restrains
 C1, C5, C10, C6
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5.a Rotating group:
 O3(H3A,H3B)
5.b Ternary CH refined with riding coordinates:
 C64(H64), C69(H69), C20(H20), C25(H25)
5.c Secondary CH2 refined with riding coordinates:
 C65(H65A,H65B), C66(H66A,H66B), C68(H68A,H68B), C67(H67A,H67B), C21(H21A,
 H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
5.d Aromatic/amide H refined with riding coordinates:
 C45(H45), C47(H47), C48(H48), C51(H51), C52(H52), C55(H55), C56(H56),
 C59(H59), C62(H62), C63(H63), C70(H70), C73(H73), C76(H76), C46(H46), C77(H77),
  C78(H78), C81(H81), C82(H82), C88(H88), C87(H87), C86(H86), C85(H85), C1(H1),
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C11(H11), C12(H12), C15(H15), C18(H18),
  C19(H19), C26(H26), C29(H29), C32(H32), C33(H33), C34(H34), C37(H37),
 C38(H38), C41(H41), C42(H42), C43(H43), C44(H44)
5.e Fitted hexagon refined as free rotating group:
 C71(C73,C74,C75,C76,C72)
5.f Naphthalene refined as free rotating group:
 C80(C79,C81,C82,C83,C84,C88,C87,C86,C85)
;
_shelx_res_checksum              10125
_shelx_hkl_checksum              43436