 
data_oc1h-dlr-cat-012-c
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C16 H11 Br I N O' 
_chemical_formula_weight          440.07

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'
 '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'
 'Br'  'Br'  -0.6763   1.2805
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'I'  'I'  -0.3257   6.8362
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_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.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    5.47070(10)
_cell_length_b                    10.91390(10)
_cell_length_c                    24.3668(3)
_cell_angle_alpha                 90
_cell_angle_beta                  95.6010(10)
_cell_angle_gamma                 90
_cell_volume                      1447.91(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     170(2)
_cell_measurement_reflns_used     2560
_cell_measurement_theta_min       3.6
_cell_measurement_theta_max       66.5
 
_exptl_crystal_description        'cut plate'
_exptl_crystal_colour             'clear colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     2.019          
_exptl_crystal_F_000              840
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.159
_exptl_crystal_size_mid           0.137
_exptl_crystal_size_min           0.063
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
   9    0  -25 0.0414
   0    1   -1 0.0495
   0    0    3 0.0429
  -9    0  -23 0.0435
  -4   -5   -7 0.0465
   0    1    0 0.0479
   0   -1    0 0.0340
   0    1   -2 0.0367
   0   -1    2 0.0265
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
 8.9994  0.0019 -25.0139  1.1386  2.1238 -1.5537
-0.4204  0.6205 -0.6005  0.0821 -0.1267  0.0372
-0.0000  0.0064  2.6413 -0.1574 -0.0469 -0.0345
-8.9992  0.0239 -22.9923  1.7289 -1.2855  2.1682
-3.8357 -4.5707 -6.8195  0.3401 -0.1689  1.3150
 0.0005  1.0000  0.0002  0.0477 -0.0940 -0.0938
-0.0005 -1.0000 -0.0002 -0.0477  0.0940  0.0938
 0.0006  1.0010 -2.0001  0.1672 -0.0591 -0.0682
-0.0006 -1.0010  2.0001 -0.1672  0.0591  0.0682
_exptl_absorpt_coefficient_mu     20.560
_exptl_absorpt_correction_T_min                     0.186
_exptl_absorpt_correction_T_max                     0.589
_exptl_absorpt_correction_type            gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min           0.407
_oxdiff_exptl_absorpt_empirical_full_max           4.862
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature 169.99(10) 
_diffrn_ambient_environment N~2~
_diffrn_source 'micro-focus sealed X-ray tube'
_diffrn_source_type 'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_monochromator mirror
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector 'Hybrid Pixel Array Detector'
_diffrn_detector_type HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number             13403
_diffrn_reflns_av_unetI/netI      0.0336
_diffrn_reflns_av_R_equivalents   0.0550
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -27
_diffrn_reflns_limit_l_max        28
_diffrn_reflns_theta_min          3.645
_diffrn_reflns_theta_max          66.482
_diffrn_reflns_theta_full         66.482
_diffrn_measured_fraction_theta_max   1.000
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    1.000
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   1.000
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              2560
_reflns_number_gt                 2434
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
_diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0394460000
_diffrn_orient_matrix_UB_12       0.0477699000
_diffrn_orient_matrix_UB_13      -0.0597073000
_diffrn_orient_matrix_UB_21       0.1873401000
_diffrn_orient_matrix_UB_22      -0.0941313000
_diffrn_orient_matrix_UB_23      -0.0175111000
_diffrn_orient_matrix_UB_31      -0.2083451000
_diffrn_orient_matrix_UB_32      -0.0936870000
_diffrn_orient_matrix_UB_33      -0.0128510000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     94.00 178.00   0.50    0.25    --  106.49  45.00 120.00  168
  2  ω     89.00 178.00   0.50    0.25    --  106.49  65.00   4.00  178
  3  ω     93.00 178.00   0.50    0.25    --  106.49  15.00 -60.00  170
  4  ω    -48.00 -14.00   0.50    0.25    --  -86.25  45.00 150.00   68
  5  ω    -65.00  25.00   0.50    0.06    --  -47.45  65.00   4.00  180
  6  ω    -75.00 -13.00   0.50    0.25    --  -86.25  65.00   4.00  124
  7  ω    -48.00 -14.00   0.50    0.25    --  -86.25  45.00 -30.00   68
  8  ω    -48.00 -14.00   0.50    0.25    --  -86.25  45.00-150.00   68
  9  ω   -120.00 -73.00   0.50    0.06    --  -47.45-125.00-180.00   94
 10  ω   -120.00 -29.00   0.50    0.06    --  -47.45 -65.00-131.00  182
 11  ω   -120.00 -32.00   0.50    0.06    --  -47.45 -57.00 -60.00  176
 12  ω   -120.00 -73.00   0.50    0.06    --  -47.45-125.00   0.00   94
 13  ω   -120.00 -32.00   0.50    0.06    --  -47.45 -57.00  30.00  176
 14  ω   -120.00 -32.00   0.50    0.06    --  -47.45 -57.00 120.00  176
 15  ω    -86.00 -13.00   0.50    0.25    --  -86.25 125.00   0.00  146
 16  ω     34.00 108.00   0.50    0.25    --  106.49 -77.00 120.00  148
 17  ω     34.00  74.00   0.50    0.25    --  106.49 -61.00 150.00   80
 18  ω     34.00  74.00   0.50    0.25    --  106.49 -61.00 -60.00   80
 19  ω    -24.00  65.00   0.50    0.06    --   47.45 -65.00-131.00  178
 20  ω     34.00  81.00   0.50    0.25    --  106.49 -65.00-131.00   94
 21  ω     34.00  74.00   0.50    0.25    --  106.49 -61.00 -90.00   80
 22  ω     34.00  74.00   0.50    0.25    --  106.49 -61.00  60.00   80
 23  ω     34.00  74.00   0.50    0.25    --  106.49 -61.00  30.00   80
;
_diffrn_measurement_method 'ω scans'
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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.
;
 
_computing_data_collection     'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement     'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction      'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution     
;
 shelXT  G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr.,
 2008, 64, 112-122.
 shelXle C. B. Huebschle, G. M. Sheldrick and B. Dittrich J. Appl. Cryst.
  (2011). 44, 1281-1284
;
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
 Diamond 4 - Crystal and Molecular Structure Visualization
  Crystal Impact - Dr. H. Putz & Dr. K. Brandenburg GbR, 
  Kreuzherrenstr. 102, 53227 Bonn, Germany
  http://www.crystalimpact.com/diamond
 Mercury CSD 2.0 - New Features for the Visualization 
 and Investigation of Crystal Structures
  C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe,
  E. Pidcock, 
  L. Rodriguez-Monge, R. Taylor, J. van de Streek and P. A. Wood, 
  J. Appl. Cryst., 41, 466-470, 2008
;
_computing_publication_material   
 'WinGX L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837-838.'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0486P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      'dual space'
_atom_sites_solution_secondary    diffmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2560
_refine_ls_number_parameters      181
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0286
_refine_ls_R_factor_gt            0.0267
_refine_ls_wR_factor_ref          0.0738
_refine_ls_wR_factor_gt           0.0725
_refine_ls_goodness_of_fit_ref    1.048
_refine_ls_restrained_S_all       1.048
_refine_ls_shift/su_max           0.005
_refine_ls_shift/su_mean          0.000
 
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 0.73431(3) 0.15090(2) 0.50019(2) 0.02363(11) Uani 1 1 d . . . . .
O1 O 0.1352(5) 0.3653(2) 0.45188(11) 0.0320(6) Uani 1 1 d . . . . .
N1 N 0.0936(5) 0.2955(3) 0.40203(12) 0.0341(7) Uani 1 1 d . . . . .
C1 C 0.6463(6) 0.2935(3) 0.55510(14) 0.0266(7) Uani 1 1 d . . . . .
C2 C 0.7697(7) 0.3165(3) 0.60563(14) 0.0309(7) Uani 1 1 d . . . . .
H2 H 0.912225 0.271212 0.618447 0.037 Uiso 1 1 calc R U . . .
C3 C 0.6784(7) 0.4093(3) 0.63785(16) 0.0354(8) Uani 1 1 d . . . . .
H3 H 0.759618 0.427343 0.673175 0.042 Uiso 1 1 calc R U . . .
C4 C 0.4695(7) 0.4750(3) 0.61845(16) 0.0362(8) Uani 1 1 d . . . . .
H4 H 0.409817 0.537559 0.640760 0.043 Uiso 1 1 calc R U . . .
C5 C 0.3485(7) 0.4509(3) 0.56747(15) 0.0308(7) Uani 1 1 d . . . . .
H5 H 0.206152 0.496425 0.554730 0.037 Uiso 1 1 calc R U . . .
C6 C 0.4356(7) 0.3590(3) 0.53448(16) 0.0279(8) Uani 1 1 d . . . . .
C7 C 0.3339(6) 0.3190(3) 0.48136(14) 0.0267(7) Uani 1 1 d . . . . .
C8 C 0.4273(6) 0.2246(3) 0.45363(13) 0.0266(7) Uani 1 1 d . . . . .
C9 C 0.2693(6) 0.2133(3) 0.40390(13) 0.0269(7) Uani 1 1 d . . . . .
C10 C 0.2765(7) 0.1256(3) 0.35648(15) 0.0322(8) Uani 1 1 d . . . . .
H10A H 0.106010 0.105035 0.342039 0.039 Uiso 1 1 calc R U . . .
H10B H 0.357734 0.048954 0.370167 0.039 Uiso 1 1 calc R U . . .
C11 C 0.4109(7) 0.1758(3) 0.30970(14) 0.0317(8) Uani 1 1 d . . . . .
C12 C 0.6049(7) 0.1111(4) 0.29100(16) 0.0417(9) Uani 1 1 d . . . . .
H12 H 0.653971 0.035359 0.307856 0.050 Uiso 1 1 calc R U . . .
C13 C 0.7285(9) 0.1557(5) 0.24791(17) 0.0484(11) Uani 1 1 d . . . . .
H13 H 0.861505 0.110802 0.235583 0.058 Uiso 1 1 calc R U . . .
C14 C 0.6578(9) 0.2649(5) 0.22324(16) 0.0501(11) Uani 1 1 d . . . . .
H14 H 0.744204 0.296405 0.194341 0.060 Uiso 1 1 calc R U . . .
C15 C 0.4624(10) 0.3287(4) 0.24024(18) 0.0509(12) Uani 1 1 d . . . . .
H15 H 0.412130 0.403258 0.222412 0.061 Uiso 1 1 calc R U . . .
C16 C 0.3379(8) 0.2854(4) 0.28321(16) 0.0400(9) Uani 1 1 d . . . . .
H16 H 0.202882 0.330175 0.294670 0.048 Uiso 1 1 calc R U . . .
Br1 Br 1.16928(6) 0.07117(3) 0.58085(2) 0.02889(12) Uani 1 1 d . . . . .
 
 
_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 C8 2.094(3) . ?
I1 C1 2.138(3) . ?
O1 C7 1.342(4) . ?
O1 N1 1.433(4) . ?
N1 C9 1.313(4) . ?
C1 C2 1.369(5) . ?
C1 C6 1.407(5) . ?
C2 C3 1.403(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.427(5) . ?
C7 C8 1.359(5) . ?
C8 C9 1.423(5) . ?
C9 C10 1.503(5) . ?
C10 C11 1.518(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.388(6) . ?
C11 C16 1.399(5) . ?
C12 C13 1.391(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.373(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
 
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
C8 I1 C1 80.89(13) . . ?
C7 O1 N1 107.8(2) . . ?
C9 N1 O1 106.2(3) . . ?
C2 C1 C6 122.9(3) . . ?
C2 C1 I1 125.1(2) . . ?
C6 C1 I1 111.9(2) . . ?
C1 C2 C3 117.7(3) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 C7 128.1(3) . . ?
C1 C6 C7 113.7(3) . . ?
O1 C7 C8 110.1(3) . . ?
O1 C7 C6 126.4(3) . . ?
C8 C7 C6 123.4(3) . . ?
C7 C8 C9 105.2(3) . . ?
C7 C8 I1 110.0(2) . . ?
C9 C8 I1 144.7(3) . . ?
N1 C9 C8 110.6(3) . . ?
N1 C9 C10 118.8(3) . . ?
C8 C9 C10 130.6(3) . . ?
C9 C10 C11 113.5(3) . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C16 118.5(4) . . ?
C12 C11 C10 120.3(3) . . ?
C16 C11 C10 121.2(4) . . ?
C11 C12 C13 120.9(4) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 120.2(4) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.1(4) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
 
_refine_diff_density_max    0.754
_refine_diff_density_min   -0.808
_refine_diff_density_rms    0.134



