Synthesis of Unsymmetrical Heterobenzisapphyrins.
Kumar, Sunit; Thorat, Kishor G.; Ravikanth, Mangalampalli; The Journal of organic chemistry 84 (2019) 417–422; doi:10.1021/acs.joc.8b02616

data_4035901
_publ_section_title
;
 Synthesis of Unsymmetrical Heterobenzisapphyrins.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              417
_journal_page_last               422
_journal_paper_doi               10.1021/acs.joc.8b02616
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C53 H38 N2 O S'
_chemical_formula_sum            'C53 H38 N2 O S'
_chemical_formula_weight         750.91
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   68.03(9)
_cell_length_b                   22.65(3)
_cell_length_c                   10.235(6)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.0630
_cell_measurement_theta_min      2.9830
_cell_volume                     15771(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_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   -110.00  19.00   0.50    8.00    --  -20.00 -72.00  36.00  258
  2  \w   -110.00  19.00   0.50    8.00    --  -20.00 -72.00-108.00  258
  3  \w    -98.00  24.00   0.50    8.00    --  -20.00   0.00-108.00  244
  4  \w   -110.00 -16.50   0.50    8.00    --  -20.00 -72.00-180.00  187
  5  \w    -59.00  70.00   0.50    8.00    --  -20.00  72.00 -36.00  258
  6  \w    -68.50 -26.00   0.50    8.00    --  -20.00 -72.00 -36.00   85
  7  \w    -53.00   3.50   0.50    8.00    --  -20.00  72.00  36.00  113
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0038508000
_diffrn_orient_matrix_UB_12      -0.0290618000
_diffrn_orient_matrix_UB_13      0.0027637000
_diffrn_orient_matrix_UB_21      -0.0095292000
_diffrn_orient_matrix_UB_22      -0.0111440000
_diffrn_orient_matrix_UB_23      0.0127606000
_diffrn_orient_matrix_UB_31      -0.0016241000
_diffrn_orient_matrix_UB_32      -0.0032524000
_diffrn_orient_matrix_UB_33      -0.0681138000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2415
_diffrn_reflns_av_unetI/netI     0.1469
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       80
_diffrn_reflns_limit_h_min       -80
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            51983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.204
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            grayish
_exptl_crystal_colour_modifier   grayish
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       plate
_exptl_crystal_F_000             6304
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 1117 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         6952
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1590
_refine_ls_R_factor_gt           0.1050
_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^)+(0.1458P)^2^+17.5588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2398
_refine_ls_wR_factor_ref         0.2863
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4168
_reflns_number_total             6952
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02616_si_002.cif
_cod_data_source_block           mr-sk-eo-1_mo_sq
_cod_original_cell_volume        15774(33)
_cod_database_code               4035901
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.971
_reflns_odcompleteness_completeness 96.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.20
_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
2.a Aromatic/amide H refined with riding coordinates:
 C49(H49), C6(H6), C36(H36), C2(H2), C51(H51), C4(H4), C35(H35), C46(H46),
 C39(H39), C14(H14), C40(H40), C42(H42), C43(H43), C13(H13), C9(H9), C18(H18),
 C50(H50), C47(H47), C3(H3), C23(H23), C24(H24), C53(H53), C52(H52), C8(H8),
 C33(H33), C32(H32), C19(H19), C28(H28), C29(H29)
2.b Idealised Me refined as rotating group:
 C45(H45A,H45B,H45C), C38(H38A,H38B,H38C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              7530
_shelx_hkl_checksum              4264
_shelx_fab_checksum              42011
_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 1.657
_oxdiff_exptl_absorpt_empirical_full_min 0.536