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

data_4517843
_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         'C9 H9 N O'
_chemical_formula_sum            'C9 H9 N O'
_chemical_formula_weight         147.18
_chemical_name_systematic        Indole-3-carbinol
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_Int_Tables_number      29
_audit_creation_date             2018-03-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   17.5632(13)
_cell_length_b                   15.4812(11)
_cell_length_c                   8.2466(5)
_cell_measurement_reflns_used    2026
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      26.6780
_cell_measurement_theta_min      2.3010
_cell_volume                     2242.2(3)
_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  'olex2.refine (Bourhis et al., 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 16.0026
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9478
_diffrn_measured_fraction_theta_max 0.9478
_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    -93.00 -21.00   1.00   22.61    --   -0.12 160.00-120.00   72
  2  \w    -14.00 106.00   1.00   90.44    --   28.61  57.00-120.00  120
  3  \w    -60.00  74.00   1.00   90.44    --   28.61 -77.00 -60.00  134
  4  \w    -20.00  29.00   1.00   90.44    --  -28.85 -99.00 150.00   49
  5  \w     49.00  94.00   1.00   22.61    --   -0.12 160.00 -90.00   45
  6  \w   -107.00 -38.00   1.00   90.44    --  -28.85 -57.00 -30.00   69
;
_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      0.0358285000
_diffrn_orient_matrix_UB_12      -0.0206129000
_diffrn_orient_matrix_UB_13      0.0308305000
_diffrn_orient_matrix_UB_21      -0.0124448000
_diffrn_orient_matrix_UB_22      0.0096466000
_diffrn_orient_matrix_UB_23      0.0801787000
_diffrn_orient_matrix_UB_31      -0.0257727000
_diffrn_orient_matrix_UB_32      -0.0333275000
_diffrn_orient_matrix_UB_33      0.0041082000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13206
_diffrn_reflns_theta_full        25.6812
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         1.75
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54884
_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    1.308
_exptl_crystal_description       plate
_exptl_crystal_F_000             936.4283
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.4590
_refine_diff_density_min         -0.3109
_refine_diff_density_rms         0.0800
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -2.1(7)
_refine_ls_d_res_high            0.8200
_refine_ls_d_res_low             11.6135
_refine_ls_goodness_of_fit_ref   1.0376
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    51
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4028
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.0373
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.0042
_refine_ls_shift/su_mean         0.0004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0769P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1680
_reflns_Friedel_coverage         0.887
_reflns_limit_h_max              21
_reflns_limit_h_min              -21
_reflns_limit_k_max              18
_reflns_limit_k_min              -18
_reflns_limit_l_max              10
_reflns_limit_l_min              -10
_reflns_number_gt                2810
_reflns_number_total             4028
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ao0c01020_si_001.cif
_cod_data_source_block           I3C
_cod_depositor_comments
'Adding full bibliography for 4517840--4517846.cif.'
_cod_original_sg_symbol_Hall     ' P 2c -2ac'
_cod_database_code               4517843
_chemical_oxdiff_formula         'C9 H9 N O'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O1-H1a = O1-C10
 0.82 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C10A(H10c,H10d), C10B(H10e,H10f)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), N1(H1), C7(H7), C6(H6), C2(H2), C5(H5), N1A(H1Aa), C7A(H7A), C5A(H5A),
  C4A(H4A), C6A(H6A), C2A(H2A), C4B(H4B), C5B(H5B), C2B(H2B), C6B(H6B),
 N1B(H1B), C7B(H7B)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1a), O1A(H1Ab), O1B(H1Ba)
;
_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 1.518
_oxdiff_exptl_absorpt_empirical_full_min 0.678