data_s5447l_twin1_hklf4
_audit_creation_date               2019-04-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/1'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C11 H10 I0.96 N O'
_chemical_formula_sum              'C11 H10 I0.96 N O'
_chemical_formula_weight           294.02
_chemical_absolute_configuration   ad
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 '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'
 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     9.8268(5)
_cell_length_b                     5.6439(3)
_cell_length_c                     9.8652(5)
_cell_angle_alpha                  90
_cell_angle_beta                   99.353(5)
_cell_angle_gamma                  90
_cell_volume                       539.86(5)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      1478
_cell_measurement_temperature      99.95(17)
_cell_measurement_theta_max        29.8390
_cell_measurement_theta_min        11.1400
_shelx_estimated_absorpt_T_max     0.959
_shelx_estimated_absorpt_T_min     0.541
_exptl_absorpt_coefficient_mu      2.818
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.64767
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.809
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               284
_exptl_crystal_size_max            0.249
_exptl_crystal_size_mid            0.017
_exptl_crystal_size_min            0.015
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0447
_diffrn_reflns_av_unetI/netI       0.0525
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.879
_diffrn_reflns_limit_h_max         13
_diffrn_reflns_limit_h_min         -12
_diffrn_reflns_limit_k_max         7
_diffrn_reflns_limit_k_min         -7
_diffrn_reflns_limit_l_max         13
_diffrn_reflns_limit_l_min         -12
_diffrn_reflns_number              3833
_diffrn_reflns_point_group_measured_fraction_full  0.997
_diffrn_reflns_point_group_measured_fraction_max  0.826
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           30.218
_diffrn_reflns_theta_min           2.092
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        99.95(17)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   10.0000
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  0.879
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -93.00 -11.00   1.00    1.00    --   -5.00  23.00  92.00   82
  2  ω    -37.00  30.00   1.00    1.00    --    7.50  23.00  92.00   67
  3  ω     46.00  95.00   1.00    1.00    --    7.50  60.00  30.00   49
  4  ω     48.00  75.00   1.00    1.00    --    7.50  30.00 -30.00   27
  5  ω    -53.00  96.00   1.00    1.00    --    7.50  50.00   0.00  149
  6  ω    -78.00  23.00   1.00    1.00    --    7.50  60.00-150.00  101
  7  ω    -38.00   6.00   1.00    1.00    --    7.50  60.00  30.00   44
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.0259207000
_diffrn_orient_matrix_UB_12        -0.0491893000
_diffrn_orient_matrix_UB_13        -0.0652702000
_diffrn_orient_matrix_UB_21        -0.0672637000
_diffrn_orient_matrix_UB_22        -0.0026364000
_diffrn_orient_matrix_UB_23        0.0173093000
_diffrn_orient_matrix_UB_31        -0.0124807000
_diffrn_orient_matrix_UB_32        0.1156624000
_diffrn_orient_matrix_UB_33        -0.0273324000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type                'Rigaku (Mo) X-ray DW Source'
_reflns_Friedel_coverage           0.720
_reflns_Friedel_fraction_full      0.994
_reflns_Friedel_fraction_max       0.763
_reflns_number_gt                  3332
_reflns_number_total               3833
_reflns_special_details
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection         'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction          'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_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)'
_refine_diff_density_max           2.561
_refine_diff_density_min           -2.481
_refine_diff_density_rms           0.307
_refine_ls_abs_structure_details
;
 Flack x determined using 940 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.02(7)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.228
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       130
_refine_ls_number_reflns           3833
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0714
_refine_ls_R_factor_gt             0.0590
_refine_ls_restrained_S_all        1.228
_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/[σ²(Fo²)+(0.1049P)²+11.8661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.2182
_refine_ls_wR_factor_ref           0.2365
_refine_special_details
;
 Refined as a 3-component twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.496(11)
 0.271(8) 0.233(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C4(H4), C1(H1), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 I1 I 0.88470(10) 0.7170(3) 0.40462(10) 0.0198(4) Uani 0.96(2) 1 d . . . . .
 O1 O 0.6135(15) 0.600(3) 0.0267(14) 0.021(3) Uani 1 1 d . . . . .
 C5 C 0.5260(16) 0.726(9) 0.2325(16) 0.016(4) Uani 1 1 d . . . . .
 C8 C 0.3071(18) 0.740(8) 0.377(2) 0.022(6) Uani 1 1 d . . . . .
 H8 H 0.232585 0.747629 0.424046 0.026 Uiso 1 1 calc R . . . .
 C4 C 0.6478(15) 0.716(8) 0.1581(15) 0.016(3) Uani 1 1 d . . . . .
 H4 H 0.681589 0.876235 0.145315 0.020 Uiso 1 1 calc R . . . .
 C11 C 0.908(3) 0.273(5) 0.112(3) 0.026(7) Uani 1 1 d . . . . .
 N1 N 0.951(3) 0.089(5) 0.113(3) 0.034(6) Uani 1 1 d . . . . .
 C3 C 0.741(2) 0.562(4) -0.019(2) 0.023(5) Uani 1 1 d . . . . .
 H3A H 0.765888 0.700744 -0.067566 0.027 Uiso 1 1 calc R . . . .
 H3B H 0.733804 0.427693 -0.081390 0.027 Uiso 1 1 calc R . . . .
 C9 C 0.320(2) 0.548(4) 0.294(2) 0.022(4) Uani 1 1 d . . . . .
 H9 H 0.256121 0.425100 0.286458 0.027 Uiso 1 1 calc R . . . .
 C1 C 0.768(2) 0.557(4) 0.227(2) 0.017(4) Uani 1 1 d . . . . .
 H1 H 0.730678 0.406293 0.252958 0.021 Uiso 1 1 calc R . . . .
 C10 C 0.432(2) 0.539(4) 0.219(2) 0.021(4) Uani 1 1 d . . . . .
 H10 H 0.442102 0.411319 0.162095 0.025 Uiso 1 1 calc R . . . .
 C2 C 0.851(2) 0.513(4) 0.109(2) 0.020(4) Uani 1 1 d . . . . .
 H2 H 0.925527 0.629275 0.114126 0.024 Uiso 1 1 calc R . . . .
 C6 C 0.512(2) 0.916(4) 0.318(2) 0.019(4) Uani 1 1 d . . . . .
 H6 H 0.575262 1.038808 0.326731 0.023 Uiso 1 1 calc R . . . .
 C7 C 0.402(2) 0.922(4) 0.392(2) 0.021(4) Uani 1 1 d . . . . .
 H7 H 0.392526 1.048162 0.450171 0.025 Uiso 1 1 calc R . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
 I1 C1 2.13(2) . ?
 O1 C4 1.44(3) . ?
 O1 C3 1.41(2) . ?
 C5 C4 1.503(19) . ?
 C5 C10 1.40(5) . ?
 C5 C6 1.38(5) . ?
 C8 H8 0.9300 . ?
 C8 C9 1.38(4) . ?
 C8 C7 1.38(4) . ?
 C4 H4 0.9800 . ?
 C4 C1 1.55(4) . ?
 C11 N1 1.12(4) . ?
 C11 C2 1.47(3) . ?
 C3 H3A 0.9700 . ?
 C3 H3B 0.9700 . ?
 C3 C2 1.55(3) . ?
 C9 H9 0.9300 . ?
 C9 C10 1.42(3) . ?
 C1 H1 0.9800 . ?
 C1 C2 1.54(3) . ?
 C10 H10 0.9300 . ?
 C2 H2 0.9800 . ?
 C6 H6 0.9300 . ?
 C6 C7 1.40(3) . ?
 C7 H7 0.9300 . ?

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
 C3 O1 C4 105.5(14) . . ?
 C10 C5 C4 119(3) . . ?
 C6 C5 C4 120(3) . . ?
 C6 C5 C10 120.7(16) . . ?
 C9 C8 H8 119.2 . . ?
 C7 C8 H8 119.2 . . ?
 C7 C8 C9 121.6(17) . . ?
 O1 C4 C5 111.6(17) . . ?
 O1 C4 H4 109.8 . . ?
 O1 C4 C1 100(2) . . ?
 C5 C4 H4 109.8 . . ?
 C5 C4 C1 115(2) . . ?
 C1 C4 H4 109.8 . . ?
 N1 C11 C2 179(4) . . ?
 O1 C3 H3A 110.2 . . ?
 O1 C3 H3B 110.2 . . ?
 O1 C3 C2 107.5(16) . . ?
 H3A C3 H3B 108.5 . . ?
 C2 C3 H3A 110.2 . . ?
 C2 C3 H3B 110.2 . . ?
 C8 C9 H9 120.3 . . ?
 C8 C9 C10 119(2) . . ?
 C10 C9 H9 120.3 . . ?
 I1 C1 H1 108.9 . . ?
 C4 C1 I1 112.7(15) . . ?
 C4 C1 H1 108.9 . . ?
 C2 C1 I1 114.2(13) . . ?
 C2 C1 C4 102.9(15) . . ?
 C2 C1 H1 108.9 . . ?
 C5 C10 C9 119(2) . . ?
 C5 C10 H10 120.6 . . ?
 C9 C10 H10 120.6 . . ?
 C11 C2 C3 113(2) . . ?
 C11 C2 C1 112.4(18) . . ?
 C11 C2 H2 109.7 . . ?
 C3 C2 H2 109.7 . . ?
 C1 C2 C3 101.7(16) . . ?
 C1 C2 H2 109.7 . . ?
 C5 C6 H6 119.9 . . ?
 C5 C6 C7 120(2) . . ?
 C7 C6 H6 119.9 . . ?
 C8 C7 C6 119(2) . . ?
 C8 C7 H7 120.3 . . ?
 C6 C7 H7 120.3 . . ?

_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  1.370
_oxdiff_exptl_absorpt_empirical_full_min  0.683
_oxdiff_twin_integration_method    simultaneous
_oxdiff_twin_items                 3
loop_
  _twin_individual_id
  _twin_individual_mass_fraction_refined
  _oxdiff_twin_reflns_isolated
  _oxdiff_twin_reflns_overlapped
  _twin_individual_twin_lattice_type
  _twin_individual_twin_matrix_11
  _twin_individual_twin_matrix_12
  _twin_individual_twin_matrix_13
  _twin_individual_twin_matrix_21
  _twin_individual_twin_matrix_22
  _twin_individual_twin_matrix_23
  _twin_individual_twin_matrix_31
  _twin_individual_twin_matrix_32
  _twin_individual_twin_matrix_33
 1 0.496(11) 47 7890 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
 1.0000
 2 0.271(8) 321 7623 nmt 0.9959 0.0007 -0.0203 0.0002 1.0005 -0.0019 0.0197
 0.0045 0.9994
 3 0.233(7) 388 7577 nmt 0.9949 -0.0363 0.0066 0.0167 1.0043 0.0002 -0.0007
 0.0023 1.0001

_twin_special_details
;
Component 2 rotated by 1.1210° 
 around [0.21 -0.98 0.03] (reciprocal) or [0.08 -1.00 0.02] (direct)
Component 3 rotated by 1.6544° 
 around [-0.12 0.01 0.99] (reciprocal) or [0.05 0.04 1.00] (direct)
;
