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

data_4517844
_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 ad
_chemical_formula_moiety         'C9 H6 N2'
_chemical_formula_sum            'C9 H6 N2'
_chemical_formula_weight         142.16
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-19
_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                   3.87758(14)
_cell_length_b                   7.6453(3)
_cell_length_c                   23.7995(9)
_cell_measurement_reflns_used    5174
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.3910
_cell_measurement_theta_min      3.7030
_cell_volume                     705.54(5)
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_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    -99.00 -34.00   1.00    1.00    --    0.00 178.00 120.00   65
  2  \w      1.00  51.00   1.00    1.00    --    0.00 -99.00 -90.00   50
  3  \w    -98.00  38.00   1.00    1.00    --  -55.02  61.00 -60.00  136
  4  \w   -151.00 -80.00   1.00    1.00    --  -55.02 -94.00  30.00   71
  5  \w   -151.00 -80.00   1.00    1.00    --  -55.02 -94.00 -90.00   71
  6  \w    -96.00  -2.00   1.00    1.00    --  -55.02 125.00  60.00   94
  7  \w   -151.00 -80.00   1.00    1.00    --  -55.02 -94.00-180.00   71
  8  \w     11.00 155.00   1.00    1.00    --   55.02  77.00   0.00  144
  9  \w     68.00 178.00   1.00    1.00    --  110.04  50.00 -30.00  110
 10  \w     57.00 150.00   1.00    1.00    --  110.04 178.00 150.00   93
 11  \w    100.00 178.00   1.00    1.00    --  110.04 111.00   0.00   78
 12  \w     64.00 178.00   1.00    1.00    --  110.04  38.00-120.00  114
 13  \w     13.00 158.00   1.00    1.00    --  110.04 -91.00-180.00  145
 14  \w    100.00 178.00   1.00    1.00    --  110.04 111.00 -90.00   78
 15  \w     18.00 115.00   1.00    1.00    --  110.04-111.00 120.00   97
 16  \w    100.00 178.00   1.00    1.00    --  110.04 111.00 150.00   78
 17  \w     66.00 178.00   1.00    1.00    --  110.04  63.00 -90.00  112
 18  \w     57.00 150.00   1.00    1.00    --  110.04 178.00  90.00   93
 19  \w     10.00 154.00   1.00    1.00    --  110.04 -77.00  60.00  144
 20  \w   -100.00  44.00   1.00    1.00    --    0.00 -77.00  30.00  144
 21  \w   -155.00 -11.00   1.00    1.00    --  -55.02 -77.00  60.00  144
 22  \w     13.00 146.00   1.00    1.00    --   55.02  45.00-150.00  133
 23  \w     11.00  38.00   1.00    1.00    --   55.02  84.00-178.50   27
 24  \w     94.00 146.00   1.00    1.00    --   55.02 125.00 120.00   52
 25  \w     13.00 146.00   1.00    1.00    --   55.02  45.00 150.00  133
 26  \w     13.00 146.00   1.00    1.00    --   55.02  45.00  30.00  133
 27  \w     11.00 155.00   1.00    1.00    --   55.02  77.00 -90.00  144
 28  \w     12.00 148.00   1.00    1.00    --   55.02  61.00 -90.00  136
 29  \w     11.00 155.00   1.00    1.00    --   55.02  77.00  60.00  144
 30  \w     67.00 157.00   1.00    1.00    --  110.04  77.00  60.00   90
 31  \w     64.00 178.00   1.00    1.00    --  110.04  38.00  30.00  114
 32  \w     66.00 178.00   1.00    1.00    --  110.04  63.00 150.00  112
 33  \w     32.00 178.00   1.00    1.00    --  110.04  25.00 120.00  146
;
_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      0.2268235000
_diffrn_orient_matrix_UB_12      0.1228674000
_diffrn_orient_matrix_UB_13      -0.0356536000
_diffrn_orient_matrix_UB_21      0.2011144000
_diffrn_orient_matrix_UB_22      0.0536503000
_diffrn_orient_matrix_UB_23      0.0530621000
_diffrn_orient_matrix_UB_31      0.2569739000
_diffrn_orient_matrix_UB_32      -0.1503988000
_diffrn_orient_matrix_UB_33      -0.0101041000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10448
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.570
_diffrn_reflns_theta_min         3.714
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73418
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 483 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0328P)^2^+0.1908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0789
_reflns_Friedel_coverage         0.602
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                1306
_reflns_number_total             1376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c01020_si_001.cif
_cod_data_source_block           4cI
_cod_depositor_comments
'Adding full bibliography for 4517840--4517846.cif.'
_cod_database_code               4517844
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C9 N1 H6'
_chemical_oxdiff_usercomment     'colourless plate, 100 K'
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.812
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C3(H3), C6(H6), C5(H5)
;
_shelx_res_checksum              5383
_shelx_hkl_checksum              735
_olex2_date_sample_data_collection 2017-09-20
_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 1.652
_oxdiff_exptl_absorpt_empirical_full_min 0.608