Transition metal-free, visible-light mediated synthesis of 1,10-phenanthroline derived ligand systems
Edwards, Alyn C.; Geist, Andreas; Müllich, Udo; Sharrad, Clint A.; Pritchard, Robin G.; Whitehead, Roger C.; Harwood, Laurence M.; Chemical Communications 53 (2017) 8160–8163; doi:10.1039/C7CC03903D

data_1546411
_publ_section_title
;
 Transition metal-free, visible-light mediated synthesis of
 1,10-phenanthroline derived ligand systems
;
_journal_issue                   58
_journal_name_full               'Chemical Communications'
_journal_page_first              8160
_journal_page_last               8163
_journal_paper_doi               10.1039/C7CC03903D
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C54 H62 N8, 1.73(H2 O), 0.3(C H4 O)'
_chemical_formula_sum            'C54.3 H66.67 N8 O2.03'
_chemical_formula_weight         863.93
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-04-05 deposited with the CCDC.
2017-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.954(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.8264(8)
_cell_length_b                   15.4605(4)
_cell_length_c                   19.2829(9)
_cell_measurement_reflns_used    6361
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.0510
_cell_measurement_theta_min      1.8070
_cell_volume                     4856.7(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.21a (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      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_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    -66.00  98.00   1.00   30.00    --   16.40  43.00 150.00  164
  2  \w    -69.00 -26.00   1.00   30.00    --   16.40  60.00   0.00   43
  3  \w     -9.00  29.00   1.00   30.00    --   16.40  60.00   0.00   38
  4  \w     58.00  90.00   1.00   30.00    --   16.40  60.00   0.00   32
  5  \w    -64.00 100.00   1.00   30.00    --   16.40  60.00-120.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0145387000
_diffrn_orient_matrix_UB_12      -0.0235618000
_diffrn_orient_matrix_UB_13      -0.0236343000
_diffrn_orient_matrix_UB_21      0.0304890000
_diffrn_orient_matrix_UB_22      -0.0196061000
_diffrn_orient_matrix_UB_23      0.0325062000
_diffrn_orient_matrix_UB_31      -0.0274879000
_diffrn_orient_matrix_UB_32      -0.0341173000
_diffrn_orient_matrix_UB_33      -0.0023593000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            38675
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.816
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.21a (Rigaku Oxford Diffraction, 2015)
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    1.182
_exptl_crystal_description       needle
_exptl_crystal_F_000             1859
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         9518
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0741
_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^)+(0.1020P)^2^+3.0970P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1937
_refine_ls_wR_factor_ref         0.2234
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5631
_reflns_number_total             9518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc03903d2.cif
_cod_data_source_block           lrgp1
_cod_original_formula_sum        'C54.30 H66.67 N8 O2.03'
_cod_database_code               1546411
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C50H50O10N4
_diffrn_oxdiff_ac3_digest_frames
;
010e8e9df0a22a45b1931eb8570dad493500441449d
;
_diffrn_oxdiff_ac3_digest_hkl
;
017bc9331c9b46472759a7a6c4bbca1eddc71c
;
_reflns_odcompleteness_completeness 99.59
_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) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C41B) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C43B)
\\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C42B) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
3. Others
 Sof(O2)=Sof(H2A)=Sof(H2B)=Sof(O6)=Sof(H6A)=Sof(H6B)=FVAR(1)
 Sof(O3)=Sof(H3A)=Sof(H3B)=Sof(O4)=Sof(H4)=Sof(C61)=Sof(H61A)=Sof(H61B)=
 Sof(H61C)=FVAR(2)
 Fixed Sof: C41(0.5) H41A(0.5) H41B(0.5) H41C(0.5) C41B(0.5) H41D(0.5)
 H41E(0.5) H41F(0.5) C42(0.5) H42A(0.5) H42B(0.5) H42C(0.5) C42B(0.5) H42D(0.5)
 H42E(0.5) H42F(0.5) C43(0.5) H43A(0.5) H43B(0.5) H43C(0.5) C43B(0.5) H43D(0.5)
 H43E(0.5) H43F(0.5)
 Fixed X: O2(0.126981) H2A(0.161461) H2B(0.091801) O3(0.105981) H3A(0.16481)
 H3B(0.064429) H1A(0.277649) H1B(0.27825) O6(0.03878) H6A(0.0909) H6B(0.00502)
 Fixed Y: O2(0.198371) H2A(0.25339) H2B(0.216529) O3(0.190761) H3A(0.185121)
 H3B(0.232479) H1A(0.35767) H1B(0.272689) O6(0.324161) H6A(0.326281)
 H6B(0.32621)
 Fixed Z: O2(0.216569) H2A(0.25012) H2B(0.16921) O3(0.25606) H3A(0.29006)
 H3B(0.2484) H1A(0.321811) H1B(0.30686) O6(0.121771) H6A(0.14286) H6B(0.06975)
4.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C47(H47A,H47B), C48(H48A,H48B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C10(H10), C25(H25), C26(H26), C28(H28), C29(H29),
 C35(H35), C36(H36), C38(H38), C39(H39)
4.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C41(H41A,
 H41B,H41C), C41B(H41D,H41E,H41F), C42(H42A,H42B,H42C), C42B(H42D,H42E,H42F),
 C43(H43A,H43B,H43C), C43B(H43D,H43E,H43F), C51(H51A,H51B,H51C), C52(H52A,H52B,
 H52C), C53(H53A,H53B,H53C), C54(H54A,H54B,H54C), C61(H61A,H61B,H61C)
4.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              21329
_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 2.851
_oxdiff_exptl_absorpt_empirical_full_min 0.494