New synthetic pathway leading to oxospirochlorins
Śniechowska, Justyna; Paluch, Piotr; Pawlak, Tomasz; Bujacz, Grzegorz D.; Danikiewicz, Witold; Potrzebowski, Marek J.; RSC Advances 8 (2018) 21354–; doi:10.1039/C8RA02445F

data_7230859
_publ_section_title
;
 New synthetic pathway leading to oxospirochlorins
;
_journal_issue                   38
_journal_name_full               'RSC Advances'
_journal_page_first              21354
_journal_paper_doi               10.1039/C8RA02445F
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C56 H37 N9 O, C H2 Cl2'
_chemical_formula_sum            'C57 H39 Cl2 N9 O'
_chemical_formula_weight         936.87
_chemical_name_common            OxoSpiro-Chlorin
_chemical_name_systematic
;
8-oxo-7-spiro((3,6-dipirydin-2-yl)-2,5-dihydro-1,2,4-triazinyl)5,10,15,20-tetraphenyl chlorin
;
_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
_audit_creation_date             2017-09-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_audit_update_record
;
2017-09-10 deposited with the CCDC.
2018-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                105.758(4)
_cell_angle_beta                 92.806(4)
_cell_angle_gamma                107.008(5)
_cell_formula_units_Z            2
_cell_length_a                   9.5173(5)
_cell_length_b                   13.2143(7)
_cell_length_c                   20.6062(10)
_cell_measurement_reflns_used    4315
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8260
_cell_measurement_theta_min      3.6420
_cell_volume                     2361.7(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.1685
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details
;
  1 omega -108.00  -76.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9774 -125.0000  -30.0000 32

  2 omega -114.00  -18.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9774  -57.0000 -150.0000 96

  3 omega -111.00  -73.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9774 -125.0000  -60.0000 38

  4 omega  -70.00   26.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9774   57.0000    0.0000 96

  5 omega   27.00   87.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9774 -125.0000  150.0000 60

  6 omega   33.00   93.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840  -94.0000 -120.0000 60

  7 omega   33.00   81.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840  -30.0000   30.0000 48

  8 omega  102.00  167.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840  125.0000  -60.0000 65

  9 omega   52.00   91.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840  -30.0000   60.0000 39

 10 omega   82.00  177.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840   45.0000    0.0000 95

 11 omega   32.00  118.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840 -125.0000    0.0000 86

 12 omega   72.00  178.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840   15.0000  -60.0000 106

 13 omega   67.00  120.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840 -125.0000 -150.0000 53

 14 omega   48.00   83.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840  -45.0000 -150.0000 35

 15 omega   38.00   91.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840  -30.0000  -30.0000 53

 16 omega   33.00  138.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840  -77.0000    0.0000 105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, TitanS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0530859000
_diffrn_orient_matrix_UB_12      -0.1025195000
_diffrn_orient_matrix_UB_13      -0.0160813000
_diffrn_orient_matrix_UB_21      0.0142962000
_diffrn_orient_matrix_UB_22      0.0057366000
_diffrn_orient_matrix_UB_23      -0.0731639000
_diffrn_orient_matrix_UB_31      0.1618630000
_diffrn_orient_matrix_UB_32      0.0760454000
_diffrn_orient_matrix_UB_33      0.0232945000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17130
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.188
_diffrn_reflns_theta_min         2.250
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.651
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            dark
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       plate
_exptl_crystal_F_000             972
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.0874
_exptl_crystal_size_min          0.0231
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.0028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     705
_refine_ls_number_reflns         9369
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0751
_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^)+(0.1234P)^2^+0.3832P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2020
_refine_ls_wR_factor_ref         0.2445
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5779
_reflns_number_total             9369
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra02445f2.cif
_cod_data_source_block           pot_por2_abs
_cod_database_code               7230859
_chemical_oxdiff_formula         'C57 H40 N9 O1 Cl2'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
 C60-Cl1 = C60-Cl2 = C60'-Cl1 = C60'-Cl2'
 1.77 with sigma of 0.001
 Cl1-Cl2 = Cl1-Cl2'
 2.93 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C33) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C38) \\sim Ueq: with sigma of 0.06 and
sigma for terminal atoms of 0.05
Uanis(C33') \\sim Ueq, Uanis(C34') \\sim Ueq, Uanis(C35') \\sim Ueq,
Uanis(C36') \\sim Ueq, Uanis(C37') \\sim Ueq, Uanis(C38') \\sim Ueq: with sigma
of 0.06 and sigma for terminal atoms of 0.05
4. Same fragment restrains
{C33, C34, C35, C36, C37, C38} sigma for 1-2: 0.02, 1-3: 0.04
as
{C33', C34', C35', C36', C37', C38'}
5. Others
 Sof(C33')=Sof(C34')=Sof(H34')=Sof(C35')=Sof(H35')=Sof(C36')=Sof(H36')=
 Sof(C37')=Sof(H37')=Sof(C38')=Sof(H38')=1-FVAR(1)
 Sof(C33)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35)=Sof(C36)=Sof(H36)=Sof(C37)=
 Sof(H37)=Sof(C38)=Sof(H38)=FVAR(1)
 Sof(C60')=Sof(H60C)=Sof(H60D)=Sof(Cl2')=1-FVAR(2)
 Sof(C60)=Sof(H60A)=Sof(H60B)=Sof(Cl2)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C60(H60A,H60B), C60'(H60C,H60D)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C12(H12), C13(H13), C17(H17), C18(H18), N6(H6), C24(H24),
 C25(H25), C26(H26), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C34(H34),
  C35(H35), C36(H36), C37(H37), C38(H38), C34'(H34'), C35'(H35'), C36'(H36'),
 C37'(H37'), C38'(H38'), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44),
 C46(H46), C47(H47), C48(H48), C49(H49), C50(H50), C52(H52), C53(H53), C54(H54),
  C55(H55), C56(H56)
;
_shelx_res_checksum              63967
_olex2_submission_special_instructions 'No special instructions were received'