Structure and Morphology of Indole Analogue Crystals.
Pisarek, Joanna; Malinska, Maura; ACS omega 5 (2020) 17141–17151; doi:10.1021/acsomega.0c01020

data_4517840
_publ_section_title
;
 Structure and Morphology of Indole Analogue Crystals.
;
_journal_issue                   28
_journal_name_full               'ACS omega'
_journal_page_first              17141
_journal_page_last               17151
_journal_paper_doi               10.1021/acsomega.0c01020
_journal_volume                  5
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C8 H7 N'
_chemical_formula_sum            'C8 H7 N'
_chemical_formula_weight         117.15
_chemical_name_systematic        Indole
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-20
_audit_creation_method
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6102(10)
_cell_length_b                   5.5255(6)
_cell_length_c                   14.639(2)
_cell_measurement_reflns_used    2607
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      30.4410
_cell_measurement_theta_min      3.9260
_cell_volume                     615.57(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0013
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     21.00  99.00   1.00   60.00    --   22.56-160.00  90.00   78
  2  \w    -43.00  46.00   1.00   60.00    --  -22.87  57.00  90.00   89
  3  \w    -96.00  50.00   1.00   60.00    --  -22.87   0.00 -90.00  146
  4  \w      1.00  91.00   1.00   60.00    --   22.56  57.00 150.00   90
  5  \w     49.00  94.00   1.00   60.00    --   22.56 160.00  30.00   45
  6  \w      1.00  91.00   1.00   60.00    --   22.56  57.00-120.00   90
  7  \w     -7.00  18.00   1.00   60.00    --   22.56  77.00 -30.00   25
  8  \w    -99.00 -36.00   1.00   60.00    --  -22.87 160.00 120.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0727187000
_diffrn_orient_matrix_UB_12      -0.0425089000
_diffrn_orient_matrix_UB_13      0.0258045000
_diffrn_orient_matrix_UB_21      -0.0252007000
_diffrn_orient_matrix_UB_22      -0.0756998000
_diffrn_orient_matrix_UB_23      -0.0368477000
_diffrn_orient_matrix_UB_31      0.0527028000
_diffrn_orient_matrix_UB_32      -0.0944817000
_diffrn_orient_matrix_UB_33      0.0179503000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6123
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.783
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44861
_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_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 427 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -10.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         1257
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0622P)^2^+0.0479P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1272
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1074
_reflns_number_total             1257
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c01020_si_001.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4517840--4517846.cif.'
_cod_original_cell_volume        615.57(14)
_cod_database_code               4517840
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C8H7N
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.963
_reflns_odcompleteness_completeness 97.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
C3A \\sim C5: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(C9) \\sim Ueq, Uanis(C9A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C7A) = Uanis(N1)
Uanis(C2A) = Uanis(C6)
Uanis(N1A) = Uanis(C7)
Uanis(C4) = Uanis(C4A)
Uanis(C9A) = Uanis(C9)
Uanis(C8A) = Uanis(C8)
Uanis(C3A) = Uanis(C5)
3. Others
 Sof(C3A)=Sof(H3A)=Sof(C2A)=Sof(H2A)=Sof(N1A)=Sof(H1A)=Sof(C8A)=Sof(C9A)=
 Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=1-
 FVAR(1)
 Sof(C3)=Sof(H3)=Sof(N1)=Sof(H1)=Sof(C9)=Sof(C8)=Sof(C7)=Sof(H7)=Sof(C6)=
 Sof(H6)=Sof(C5)=Sof(H5)=Sof(C4)=Sof(H4)=Sof(C2)=Sof(H2)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), N1(H1), C7(H7), C6(H6), C5(H5), C4(H4), C2(H2), C3A(H3A), C2A(H2A),
 N1A(H1A), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A)
4.b Fitted hexagon refined as free rotating group:
 C9(C8,C7,C6,C5,C4), C8A(C9A,C4A,C5A,C6A,C7A)
;
_olex2_date_sample_data_collection 2017-11-29
_olex2_submission_original_sample_id Indole
_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 6.641
_oxdiff_exptl_absorpt_empirical_full_min 0.269