 
data_mpc_507_02
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H16 B F2 N3 O S2'
_chemical_formula_weight          427.29
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'B'  'B'   0.0090   0.0039
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0311   0.0180
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0492   0.0322
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F'  'F'   0.0727   0.0534
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.3331   0.5567
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            orthorhombic
_symmetry_space_group_name_H-M    P212121
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 
_cell_length_a                    5.4633(2)
_cell_length_b                    7.9239(4)
_cell_length_c                    42.334(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1832.65(14)
_cell_formula_units_Z             4
_cell_measurement_temperature   100.01(10) 
_cell_measurement_reflns_used   4085
_cell_measurement_theta_min     4.1780
_cell_measurement_theta_max     69.9660
 
_exptl_crystal_description        needle
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.4
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.549
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              880
_exptl_absorpt_coefficient_mu     2.970
_exptl_absorpt_correction_T_min                   0.75437
_exptl_absorpt_correction_T_max                   1.00000
_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_special_details
;
 ?
;
 
_diffrn_ambient_temperature 100.01(10) 
_diffrn_radiation_wavelength      1.54184
_diffrn_radiation_type            CuK\a
_diffrn_radiation_source          'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator   mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             8140
_diffrn_reflns_av_R_equivalents   0.0330
_diffrn_reflns_av_sigmaI/netI     0.0377
_diffrn_reflns_limit_h_min        -4
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -42
_diffrn_reflns_limit_l_max        51
_diffrn_reflns_theta_min          4.18
_diffrn_reflns_theta_max          69.95
_reflns_number_total              3234
_reflns_number_gt                 3110
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0666P)²+3.1125P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.00(3)
_refine_ls_number_reflns          3234
_refine_ls_number_parameters      308
_refine_ls_number_restraints      68
_refine_ls_R_factor_all           0.0604
_refine_ls_R_factor_gt            0.0554
_refine_ls_wR_factor_ref          0.1396
_refine_ls_wR_factor_gt           0.1378
_refine_ls_goodness_of_fit_ref    1.065
_refine_ls_restrained_S_all       1.056
_refine_ls_shift/su_max           0.046
_refine_ls_shift/su_mean          0.004
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.90509(19) 0.94760(14) 0.10473(2) 0.0321(3) Uani 1 1 d . . .
F1 F 0.5401(5) 1.4722(3) 0.12267(5) 0.0346(6) Uani 1 1 d . . .
F2 F 0.1965(4) 1.3146(3) 0.12727(5) 0.0322(6) Uani 1 1 d . . .
N1 N 0.8158(7) 1.1995(5) 0.30964(8) 0.0347(8) Uani 1 1 d . . .
N2 N 0.8030(6) 1.0928(4) 0.16008(7) 0.0285(7) Uani 1 1 d . . .
N3 N 0.5746(6) 1.1725(4) 0.11455(7) 0.0234(7) Uani 1 1 d . . .
O1 O 0.4949(5) 1.2928(4) 0.16644(6) 0.0313(7) Uani 1 1 d . . .
B1 B 0.4436(9) 1.3198(6) 0.13220(11) 0.0292(10) Uani 1 1 d . . .
C1 C 1.0118(9) 1.1025(6) 0.32340(10) 0.0398(11) Uani 1 1 d . . .
H1A H 1.0091 1.1153 0.3459 0.060 Uiso 1 1 calc R . .
H1B H 1.1658 1.1418 0.3153 0.060 Uiso 1 1 calc R . .
H1C H 0.9912 0.9855 0.3181 0.060 Uiso 1 1 calc R . .
C2 C 0.6696(9) 1.3037(6) 0.33078(9) 0.0387(11) Uani 1 1 d . . .
H2A H 0.7207 1.2849 0.3522 0.058 Uiso 1 1 calc R . .
H2B H 0.5000 1.2743 0.3286 0.058 Uiso 1 1 calc R . .
H2C H 0.6918 1.4204 0.3255 0.058 Uiso 1 1 calc R . .
C3 C 0.7803(8) 1.2021(5) 0.27756(9) 0.0262(8) Uani 1 1 d . . .
C4 C 0.9341(8) 1.1077(5) 0.25737(9) 0.0295(9) Uani 1 1 d . . .
H4 H 1.0614 1.0447 0.2659 0.035 Uiso 1 1 calc R . .
C5 C 0.8977(8) 1.1077(5) 0.22509(9) 0.0276(8) Uani 1 1 d . . .
H5 H 1.0015 1.0449 0.2122 0.033 Uiso 1 1 calc R . .
C6 C 0.7077(7) 1.2005(5) 0.21138(9) 0.0262(8) Uani 1 1 d . . .
C7 C 0.5546(7) 1.2941(5) 0.23124(9) 0.0270(8) Uani 1 1 d . . .
H7 H 0.4267 1.3561 0.2225 0.032 Uiso 1 1 calc R . .
C8 C 0.5898(8) 1.2960(5) 0.26351(9) 0.0299(9) Uani 1 1 d . . .
H8 H 0.4865 1.3602 0.2762 0.036 Uiso 1 1 calc R . .
C9 C 0.6671(7) 1.1966(5) 0.17744(9) 0.0244(8) Uani 1 1 d . . .
C10 C 0.7489(7) 1.0854(5) 0.12909(9) 0.0245(8) Uani 1 1 d . . .
C11 C 0.7260(7) 1.0116(5) 0.07287(9) 0.0259(8) Uani 1 1 d . . .
C12 C 0.5559(7) 1.1314(5) 0.08234(8) 0.0216(8) Uani 1 1 d . . .
C13 C 0.3844(8) 1.1944(5) 0.06108(9) 0.0270(8) Uani 1 1 d . . .
H13 H 0.2664 1.2719 0.0674 0.032 Uiso 1 1 calc R . .
C14 C 0.3956(7) 1.1377(5) 0.03002(9) 0.0254(8) Uani 1 1 d . A .
H14 H 0.2830 1.1793 0.0155 0.031 Uiso 1 1 calc R . .
C15 C 0.5695(7) 1.0208(5) 0.01985(9) 0.0237(8) Uani 1 1 d . . .
C16 C 0.7373(7) 0.9566(5) 0.04131(9) 0.0250(8) Uani 1 1 d D A .
H16 H 0.8549 0.8788 0.0350 0.030 Uiso 1 1 calc R . .
C17 C 0.588(3) 0.966(3) -0.01457(15) 0.0231(10) Uani 0.684(5) 1 d PDU A 1
S2 S 0.3682(5) 1.0306(5) -0.04054(5) 0.0274(5) Uani 0.684(5) 1 d PDU A 1
C18 C 0.771(3) 0.880(2) -0.0278(3) 0.0238(10) Uani 0.684(5) 1 d PDU A 1
H18 H 0.9083 0.8421 -0.0169 0.029 Uiso 0.684(5) 1 calc PR A 1
C19 C 0.7281(12) 0.8505(11) -0.06158(16) 0.0239(9) Uani 0.684(5) 1 d PDU A 1
H19 H 0.8297 0.7881 -0.0748 0.029 Uiso 0.684(5) 1 calc PR A 1
C20 C 0.5149(12) 0.9296(10) -0.07084(16) 0.0239(9) Uani 0.684(5) 1 d PDU A 1
H20 H 0.4568 0.9283 -0.0915 0.029 Uiso 0.684(5) 1 calc PR A 1
C17A C 0.568(6) 0.977(5) -0.0135(3) 0.021(2) Uani 0.316(5) 1 d PDU A 2
S2A S 0.7948(15) 0.8528(10) -0.02850(18) 0.0308(15) Uani 0.316(5) 1 d PDU A 2
C18A C 0.400(5) 1.015(4) -0.0354(4) 0.026(2) Uani 0.316(5) 1 d PDU A 2
H18A H 0.2572 1.0737 -0.0305 0.031 Uiso 0.316(5) 1 calc PR A 2
C19A C 0.455(3) 0.959(2) -0.0677(4) 0.029(2) Uani 0.316(5) 1 d PDU A 2
H19A H 0.3638 0.9791 -0.0859 0.035 Uiso 0.316(5) 1 calc PR A 2
C20A C 0.671(3) 0.868(2) -0.0654(3) 0.030(2) Uani 0.316(5) 1 d PDU A 2
H20A H 0.7445 0.8187 -0.0829 0.036 Uiso 0.316(5) 1 calc PR A 2
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 C10 1.727(4) . ?
S1 C11 1.741(4) . ?
F1 B1 1.378(5) . ?
F2 B1 1.367(5) . ?
N1 C3 1.372(5) . ?
N1 C1 1.441(6) . ?
N1 C2 1.456(6) . ?
N2 C9 1.330(5) . ?
N2 C10 1.346(5) . ?
N3 C10 1.327(5) . ?
N3 C12 1.406(5) . ?
N3 B1 1.560(5) . ?
O1 C9 1.297(5) . ?
O1 B1 1.492(5) . ?
C3 C8 1.411(6) . ?
C3 C4 1.413(6) . ?
C4 C5 1.381(5) . ?
C5 C6 1.398(6) . ?
C6 C7 1.399(5) . ?
C6 C9 1.454(5) . ?
C7 C8 1.380(5) . ?
C11 C12 1.388(5) . ?
C11 C16 1.407(5) . ?
C12 C13 1.392(5) . ?
C13 C14 1.391(5) . ?
C14 C15 1.395(5) . ?
C15 C16 1.387(5) . ?
C15 C17A 1.455(9) . ?
C15 C17 1.524(6) . ?
C17 C18 1.334(15) . ?
C17 S2 1.707(7) . ?
S2 C20 1.711(6) . ?
C18 C19 1.467(15) . ?
C19 C20 1.380(7) . ?
C17A C18A 1.341(17) . ?
C17A S2A 1.703(13) . ?
S2A C20A 1.706(10) . ?
C18A C19A 1.471(17) . ?
C19A C20A 1.385(10) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C10 S1 C11 90.05(19) . . ?
C3 N1 C1 120.9(4) . . ?
C3 N1 C2 121.5(4) . . ?
C1 N1 C2 117.5(3) . . ?
C9 N2 C10 116.3(3) . . ?
C10 N3 C12 112.4(3) . . ?
C10 N3 B1 119.7(3) . . ?
C12 N3 B1 127.2(3) . . ?
C9 O1 B1 124.7(3) . . ?
F2 B1 F1 111.1(4) . . ?
F2 B1 O1 109.3(4) . . ?
F1 B1 O1 109.8(3) . . ?
F2 B1 N3 110.9(3) . . ?
F1 B1 N3 109.9(3) . . ?
O1 B1 N3 105.8(3) . . ?
N1 C3 C8 122.0(4) . . ?
N1 C3 C4 120.4(4) . . ?
C8 C3 C4 117.6(3) . . ?
C5 C4 C3 120.9(4) . . ?
C4 C5 C6 121.2(4) . . ?
C5 C6 C7 118.3(4) . . ?
C5 C6 C9 120.8(3) . . ?
C7 C6 C9 120.9(4) . . ?
C8 C7 C6 121.2(4) . . ?
C7 C8 C3 121.0(4) . . ?
O1 C9 N2 124.7(3) . . ?
O1 C9 C6 117.0(3) . . ?
N2 C9 C6 118.3(3) . . ?
N3 C10 N2 125.9(3) . . ?
N3 C10 S1 114.0(3) . . ?
N2 C10 S1 120.1(3) . . ?
C12 C11 C16 121.0(3) . . ?
C12 C11 S1 110.6(3) . . ?
C16 C11 S1 128.4(3) . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 N3 113.0(3) . . ?
C13 C12 N3 126.4(3) . . ?
C14 C13 C12 117.8(4) . . ?
C13 C14 C15 122.4(4) . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 C17A 123.5(6) . . ?
C14 C15 C17A 117.0(6) . . ?
C16 C15 C17 118.6(4) . . ?
C14 C15 C17 121.9(4) . . ?
C17A C15 C17 4.9(7) . . ?
C15 C16 C11 118.7(3) . . ?
C18 C17 C15 126.7(9) . . ?
C18 C17 S2 114.2(7) . . ?
C15 C17 S2 119.0(5) . . ?
C20 S2 C17 90.8(4) . . ?
C17 C18 C19 111.8(12) . . ?
C20 C19 C18 109.8(9) . . ?
C19 C20 S2 113.3(6) . . ?
C18A C17A C15 128.3(14) . . ?
C18A C17A S2A 111.9(11) . . ?
C15 C17A S2A 119.7(7) . . ?
C20A S2A C17A 90.6(7) . . ?
C17A C18A C19A 115.7(19) . . ?
C20A C19A C18A 105.4(17) . . ?
C19A C20A S2A 116.1(13) . . ?
 
_diffrn_measured_fraction_theta_max    0.991
_diffrn_reflns_theta_full              69.95
_diffrn_measured_fraction_theta_full   0.991
_refine_diff_density_max    0.844
_refine_diff_density_min   -0.296
_refine_diff_density_rms    0.077
