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

data_4517842
_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_formula_moiety         'C9 H9 N O'
_chemical_formula_sum            'C9 H9 N O'
_chemical_formula_weight         147.17
_chemical_name_systematic        1H-indole-2-methanol
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_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                 95.078(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.6942(6)
_cell_length_b                   5.3788(4)
_cell_length_c                   31.905(2)
_cell_measurement_reflns_used    1845
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      70.2670
_cell_measurement_theta_min      7.1950
_cell_volume                     1486.16(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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    -42.00  92.00   1.00    1.00    --    0.00  57.00-180.00  134
  2  \w      1.00  51.00   1.00    1.00    --    0.00 -99.00 150.00   50
  3  \w   -151.00 -80.00   1.00    1.00    --  -55.02 -94.00 -30.00   71
  4  \w   -146.00 -73.00   1.00    1.00    --  -55.02-125.00   0.00   73
  5  \w     94.00 146.00   1.00    1.00    --   55.02 125.00  30.00   52
  6  \w     23.00 121.00   1.00    1.00    --   55.02-125.00  60.00   98
  7  \w     94.00 146.00   1.00    1.00    --   55.02 125.00  90.00   52
  8  \w    -45.00 155.00   1.00    1.00    --   55.02   0.00 120.00  200
  9  \w     94.00 146.00   1.00    1.00    --   55.02 125.00-180.00   52
 10  \w     94.00 146.00   1.00    1.00    --   55.02 125.00 -30.00   52
 11  \w    100.00 178.00   1.00    1.00    --  110.04 111.00   0.00   78
 12  \w    100.00 178.00   1.00    1.00    --  110.04 111.00 -60.00   78
 13  \w     18.00 115.00   1.00    1.00    --  110.04-111.00  30.00   97
 14  \w     32.00 178.00   1.00    1.00    --  110.04  25.00  30.00  146
 15  \w     18.00 115.00   1.00    1.00    --  110.04-111.00-120.00   97
 16  \w     68.00 178.00   1.00    1.00    --  110.04  50.00  90.00  110
 17  \w    100.00 178.00   1.00    1.00    --  110.04 111.00  30.00   78
 18  \w     68.00 178.00   1.00    1.00    --  110.04  50.00-120.00  110
 19  \w     18.00 115.00   1.00    1.00    --  110.04-111.00 150.00   97
 20  \w    100.00 178.00   1.00    1.00    --  110.04 111.00 -90.00   78
 21  \w     57.00 150.00   1.00    1.00    --  110.04 178.00  60.00   93
 22  \w    100.00 178.00   1.00    1.00    --  110.04 111.00  60.00   78
 23  \w     10.00 136.00   1.00    1.00    --  110.04 -77.00  30.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0084985000
_diffrn_orient_matrix_UB_12      -0.1257920000
_diffrn_orient_matrix_UB_13      -0.0430822000
_diffrn_orient_matrix_UB_21      -0.0080174000
_diffrn_orient_matrix_UB_22      0.2566988000
_diffrn_orient_matrix_UB_23      -0.0215614000
_diffrn_orient_matrix_UB_31      0.1775280000
_diffrn_orient_matrix_UB_32      0.0170918000
_diffrn_orient_matrix_UB_33      0.0054057000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            12482
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.060
_diffrn_reflns_theta_min         2.781
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.562
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0556
_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^)+(0.0729P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1569
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1852
_reflns_number_total             2839
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c01020_si_001.cif
_cod_data_source_block           I2M
_cod_depositor_comments
'Adding full bibliography for 4517840--4517846.cif.'
_cod_original_cell_volume        1486.18(18)
_cod_database_code               4517842
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C9H8NO
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.696
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H10C,H10D} of C10, {H10A,H10B} of C10A, All N(H) groups
 At 1.5 times of:
  All O(H) groups, {H1AC,H1A} of C3
2. Restrained distances
 O1-H1AC
 0.82 with sigma of 0.001
3. Others
 Fixed Sof: H1AA(0.5) H1B(0.5) H1AC(0.5) H1A(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C10A(H10A,H10B), C10(H10C,H10D)
4.b Aromatic/amide H refined with riding coordinates:
 N1A(H1AB), C6A(H6A), C7A(H7A), C3A(H3A), C5A(H5A), C4A(H4A), N1(H1), C5(H5),
 C4(H4), C7(H7), C6(H6), C3(H3)
4.c Idealised tetrahedral OH refined as rotating group:
 O1A(H1AA), O1(H1B)
;
_shelx_res_checksum              20386
_shelx_hkl_checksum              42419
_olex2_date_sample_data_collection 2017-11-03
_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 2.067
_oxdiff_exptl_absorpt_empirical_full_min 0.577