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

data_4517841
_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         '1(C9 H9 N)'
_chemical_formula_sum            'C9 H9 N'
_chemical_formula_weight         131.17
_chemical_name_systematic        7-Methylindole
_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                   9.3176(7)
_cell_length_b                   5.2878(4)
_cell_length_c                   14.2479(13)
_cell_measurement_reflns_used    2534
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.6630
_cell_measurement_theta_min      4.0970
_cell_volume                     701.99(10)
_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 8.0013
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.979
_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     -3.00  88.00   1.00   45.01    --   18.75  57.00 150.00   91
  2  \w     -7.00  91.00   1.00   45.01    --   18.75  37.00 -60.00   98
  3  \w    -25.00  92.00   1.00   45.01    --   18.75  19.00  90.00  117
  4  \w    -20.00  61.00   1.00   45.01    --   18.75 -99.00   0.00   81
  5  \w    -95.00 -21.00   1.00   45.01    --  -19.06 160.00 150.00   74
  6  \w    -89.00 -43.00   1.00   45.01    --  -19.06 -77.00 -60.00   46
  7  \w    -95.00 -21.00   1.00   45.01    --  -19.06 160.00  30.00   74
;
_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      -0.0512850000
_diffrn_orient_matrix_UB_12      0.0333092000
_diffrn_orient_matrix_UB_13      0.0346860000
_diffrn_orient_matrix_UB_21      -0.0443780000
_diffrn_orient_matrix_UB_22      0.0535214000
_diffrn_orient_matrix_UB_23      -0.0352008000
_diffrn_orient_matrix_UB_31      -0.0345298000
_diffrn_orient_matrix_UB_32      -0.1183996000
_diffrn_orient_matrix_UB_33      -0.0061305000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7458
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.248
_diffrn_reflns_theta_min         4.111
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46958
_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    1.241
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details
;
 Flack x determined using 511 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1657
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0253P)^2^+0.0765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0890
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                1300
_reflns_number_total             1657
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c01020_si_001.cif
_cod_data_source_block           7mI
_cod_depositor_comments
'Adding full bibliography for 4517840--4517846.cif.'
_cod_original_cell_volume        701.98(10)
_cod_database_code               4517841
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C9 H9 N'
_chemical_oxdiff_usercomment     '100 K, colourless block'
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.978
_reflns_odcompleteness_completeness 99.55
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C6A) = Uanis(C5A)
Uanis(C8) = Uanis(C8A)
Uanis(C10A) = Uanis(C7A)
3. Others
 Sof(C7A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C10A)=Sof(H10D)=Sof(H10E)=
 Sof(H10F)=Sof(C9A)=Sof(C8A)=Sof(N1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=
 Sof(H3A)=Sof(C6A)=Sof(H6A)=1-FVAR(1)
 Sof(N1)=Sof(H1)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C9)=Sof(C8)=
 Sof(C7)=Sof(C6)=Sof(H6)=Sof(C5)=Sof(H5)=Sof(C4)=Sof(H4)=Sof(C2)=Sof(H2)=
 Sof(C3)=Sof(H3)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C5(H5), C4(H4), C2(H2), C3(H3), C4A(H4A), C5A(H5A), N1A(H1A),
 C2A(H2A), C3A(H3A), C6A(H6A)
4.b Fitted pentagon refined as free rotating group:
 C9A(C8A,N1A,C2A,C3A)
4.c Fitted hexagon refined as free rotating group:
 C9(C8,C7,C6,C5,C4)
4.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C10A(H10D,H10E,H10F)
;
_olex2_date_sample_data_collection 2017-12-06
_olex2_submission_original_sample_id 7-Methylindole
_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 1.512
_oxdiff_exptl_absorpt_empirical_full_min 0.650