Enantioselective oxidative coupling reaction of 2-naphthol derivatives catalyzed by chiral diphosphine oxide–iron(II) complexes
Horibe, Takahiro; Nakagawa, Keita; Hazeyama, Takashi; Takeda, Kazuki; Ishihara, Kazuaki; Chemical Communications  (2019) –; doi:10.1039/C9CC07834G

data_7124342
_publ_section_title
;
 Enantioselective oxidative coupling reaction of 2-naphthol derivatives
 catalyzed by chiral diphosphine oxide--iron(II) complexes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07834G
_journal_year                    2019
_chemical_formula_moiety         'C89 H68 Fe O5 P4, 2(C F3 O3 S), 2(C H4 O)'
_chemical_formula_sum            'C93 H76 F6 Fe O13 P4 S2'
_chemical_formula_weight         1759.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-14
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-12-22 deposited with the CCDC.    2019-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                98.365(3)
_cell_angle_beta                 100.634(4)
_cell_angle_gamma                113.523(4)
_cell_formula_units_Z            2
_cell_length_a                   15.5435(7)
_cell_length_b                   15.7355(5)
_cell_length_c                   22.4546(8)
_cell_measurement_reflns_used    13985
_cell_measurement_temperature    93
_cell_measurement_theta_max      28.0860
_cell_measurement_theta_min      2.1070
_cell_volume                     4800.6(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      93
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.889
_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   -105.00  75.00   0.50   15.00    --  -15.00  45.00   0.00  360
  2  \w   -105.00  75.00   0.50   15.00    --  -15.00  45.00  90.00  360
  3  \w   -105.00  75.00   0.50   15.00    --  -15.00  45.00 180.00  360
  4  \w   -105.00  75.00   0.50   15.00    --  -15.00  45.00 270.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0053355000
_diffrn_orient_matrix_UB_12      -0.0241773000
_diffrn_orient_matrix_UB_13      0.0243666000
_diffrn_orient_matrix_UB_21      0.0505312000
_diffrn_orient_matrix_UB_22      0.0266821000
_diffrn_orient_matrix_UB_23      0.0147369000
_diffrn_orient_matrix_UB_31      -0.0092664000
_diffrn_orient_matrix_UB_32      0.0356692000
_diffrn_orient_matrix_UB_33      0.0169411000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1129
_diffrn_reflns_av_unetI/netI     0.1833
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            87871
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.753
_diffrn_reflns_theta_min         1.557
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       plate
_exptl_crystal_F_000             1820
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         2.188
_refine_diff_density_min         -1.493
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1080
_refine_ls_number_reflns         26633
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1833
_refine_ls_R_factor_gt           0.1094
_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^)+(0.1903P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3067
_refine_ls_wR_factor_ref         0.3485
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13217
_reflns_number_total             26633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07834g2.cif
_cod_data_source_block           20181213-
_cod_original_cell_volume        4800.6(3)
_cod_database_code               7124342
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.924
_reflns_odcompleteness_completeness 88.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.68
_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, All O(H) groups
2. Restrained distances
 O00C-H00C
 0.85 with sigma of 0.01
 C031-H00C
 1.924674 with sigma of 0.02
 Fe01-H00C
 2.578985 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
S007: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 S007
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Aromatic/amide H refined with riding coordinates:
 C00P(H00P), C00R(H00R), C00T(H00T), C00X(H00X), C00Y(H00Y), C00Z(H00Z),
 C012(H012), C013(H013), C014(H014), C015(H015), C017(H017), C018(H018),
 C019(H019), C01B(H01B), C01C(H01C), C01D(H01D), C01E(H01E), C01G(H01G),
 C01J(H01J), C01K(H01K), C01L(H01L), C01M(H01M), C01N(H01N), C01O(H01O),
 C01P(H01P), C01Q(H01Q), C01R(H01R), C01S(H01S), C01T(H01T), C01W(H01W),
 C01X(H01X), C01Y(H01Y), C01Z(H01Z), C020(H020), C021(H021), C022(H022),
 C023(H023), C024(H024), C025(H025), C026(H026), C027(H027), C028(H028),
 C029(H029), C02B(H02B), C02C(H02C), C02D(H02D), C02E(H02E), C02F(H02F),
 C02G(H02G), C02H(H02H), C02I(H02I), C02K(H02K), C02L(H02L), C02M(H02M),
 C02N(H02N), C02P(H02P), C02R(H02R), C02S(H02S), C02T(H02T), C02V(H02V),
 C02W(H02W), C02X(H02X), C02Y(H02Y), C030(H030)
5.b Idealised Me refined as rotating group:
 C02A(H02A,H02J,H02O), C02O(H02Q,H02U,H02Z), C031(H03A,H03B,H03C)
5.c Idealised tetrahedral OH refined as rotating group:
 O00D(H00D), O00E(H00E)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.845
_oxdiff_exptl_absorpt_empirical_full_min 0.510