#------------------------------------------------------------------------------
#$Date: 2020-09-02 09:26:05 +0300 (Wed, 02 Sep 2020) $
#$Revision: 255799 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/78/4517842.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4517842
loop_
_publ_author_name
'Pisarek, Joanna'
'Malinska, Maura'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -42.00  92.00   1.00    1.00    --    0.00  57.00-180.00  134
  2  ω      1.00  51.00   1.00    1.00    --    0.00 -99.00 150.00   50
  3  ω   -151.00 -80.00   1.00    1.00    --  -55.02 -94.00 -30.00   71
  4  ω   -146.00 -73.00   1.00    1.00    --  -55.02-125.00   0.00   73
  5  ω     94.00 146.00   1.00    1.00    --   55.02 125.00  30.00   52
  6  ω     23.00 121.00   1.00    1.00    --   55.02-125.00  60.00   98
  7  ω     94.00 146.00   1.00    1.00    --   55.02 125.00  90.00   52
  8  ω    -45.00 155.00   1.00    1.00    --   55.02   0.00 120.00  200
  9  ω     94.00 146.00   1.00    1.00    --   55.02 125.00-180.00   52
 10  ω     94.00 146.00   1.00    1.00    --   55.02 125.00 -30.00   52
 11  ω    100.00 178.00   1.00    1.00    --  110.04 111.00   0.00   78
 12  ω    100.00 178.00   1.00    1.00    --  110.04 111.00 -60.00   78
 13  ω     18.00 115.00   1.00    1.00    --  110.04-111.00  30.00   97
 14  ω     32.00 178.00   1.00    1.00    --  110.04  25.00  30.00  146
 15  ω     18.00 115.00   1.00    1.00    --  110.04-111.00-120.00   97
 16  ω     68.00 178.00   1.00    1.00    --  110.04  50.00  90.00  110
 17  ω    100.00 178.00   1.00    1.00    --  110.04 111.00  30.00   78
 18  ω     68.00 178.00   1.00    1.00    --  110.04  50.00-120.00  110
 19  ω     18.00 115.00   1.00    1.00    --  110.04-111.00 150.00   97
 20  ω    100.00 178.00   1.00    1.00    --  110.04 111.00 -90.00   78
 21  ω     57.00 150.00   1.00    1.00    --  110.04 178.00  60.00   93
 22  ω    100.00 178.00   1.00    1.00    --  110.04 111.00  60.00   78
 23  ω     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       'ω 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/[σ²(Fo²)+(0.0729P)²] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 1.1288(2) 0.5095(3) 0.73035(6) 0.0343(4) Uani 1 1 d . . . . .
H1AA H 1.043974 0.494128 0.739422 0.051 Uiso 0.5 1 calc GR . P A -1
N1A N 0.9808(2) 0.7542(4) 0.62699(6) 0.0279(5) Uani 1 1 d . . . . .
H1AB H 1.027821 0.890902 0.622421 0.033 Uiso 1 1 calc R . . . .
C8A C 0.8723(2) 0.6402(4) 0.59929(7) 0.0250(5) Uani 1 1 d . . . . .
C2A C 1.0019(3) 0.6140(4) 0.66311(8) 0.0272(5) Uani 1 1 d . . . . .
C6A C 0.7055(3) 0.5560(4) 0.53798(8) 0.0306(6) Uani 1 1 d . . . . .
H6A H 0.665143 0.597638 0.510922 0.037 Uiso 1 1 calc R . . . .
C7A C 0.8155(3) 0.7087(4) 0.55873(8) 0.0283(5) Uani 1 1 d . . . . .
H7A H 0.850099 0.851525 0.546096 0.034 Uiso 1 1 calc R . . . .
C9A C 0.8222(2) 0.4238(4) 0.61908(7) 0.0236(5) Uani 1 1 d . . . . .
C3A C 0.9067(2) 0.4125(4) 0.65989(7) 0.0264(5) Uani 1 1 d . . . . .
H3A H 0.897962 0.290636 0.680221 0.032 Uiso 1 1 calc R . . . .
C5A C 0.6537(3) 0.3403(4) 0.55685(8) 0.0306(6) Uani 1 1 d . . . . .
H5A H 0.579730 0.241213 0.542130 0.037 Uiso 1 1 calc R . . . .
C4A C 0.7112(3) 0.2719(4) 0.59721(8) 0.0267(5) Uani 1 1 d . . . . .
H4A H 0.676653 0.127939 0.609509 0.032 Uiso 1 1 calc R . . . .
N1 N 0.5056(2) 0.2293(4) 0.36502(6) 0.0272(5) Uani 1 1 d . . . . .
H1 H 0.456538 0.365499 0.368509 0.033 Uiso 1 1 calc R . . . .
C8 C 0.6164(3) 0.1286(4) 0.39336(8) 0.0257(5) Uani 1 1 d . . . . .
C5 C 0.8398(3) -0.1522(4) 0.43809(8) 0.0305(6) Uani 1 1 d . . . . .
H5 H 0.915581 -0.244236 0.453550 0.037 Uiso 1 1 calc R . . . .
C9 C 0.6691(3) -0.0934(4) 0.37535(8) 0.0258(5) Uani 1 1 d . . . . .
C4 C 0.7829(3) -0.2348(4) 0.39880(8) 0.0278(5) Uani 1 1 d . . . . .
H4 H 0.819292 -0.381780 0.387923 0.033 Uiso 1 1 calc R . . . .
C7 C 0.6734(3) 0.2103(4) 0.43329(8) 0.0284(5) Uani 1 1 d . . . . .
H7 H 0.637241 0.355683 0.444752 0.034 Uiso 1 1 calc R . . . .
C6 C 0.7855(3) 0.0673(4) 0.45513(8) 0.0304(6) Uani 1 1 d . . . . .
H6 H 0.825771 0.117968 0.481733 0.036 Uiso 1 1 calc R . . . .
C2 C 0.4852(3) 0.0776(4) 0.33002(8) 0.0276(5) Uani 1 1 d . . . . .
O1 O 0.38878(19) 0.3692(3) 0.27645(6) 0.0337(4) Uani 1 1 d D . . . .
H1B H 0.309849 0.412471 0.262369 0.050 Uiso 0.5 1 calc GR . P B -1
C10A C 1.1195(3) 0.6899(5) 0.69771(8) 0.0336(6) Uani 1 1 d . . . . .
H10A H 1.219485 0.707035 0.686709 0.040 Uiso 1 1 calc R . . . .
H10B H 1.091452 0.849701 0.708876 0.040 Uiso 1 1 calc R . . . .
C10 C 0.3638(3) 0.1330(5) 0.29556(8) 0.0333(6) Uani 1 1 d . . . . .
H10C H 0.363383 0.003624 0.274364 0.040 Uiso 1 1 calc R . . . .
H10D H 0.263609 0.133024 0.306733 0.040 Uiso 1 1 calc R . . . .
C3 C 0.5833(3) -0.1199(4) 0.33521(7) 0.0280(5) Uani 1 1 d . . . . .
H3 H 0.592778 -0.248516 0.316122 0.034 Uiso 1 1 calc R . . . .
H1AC H 0.465(3) 0.374(9) 0.2631(11) 0.042 Uiso 0.5 1 d DR . P C -2
H1A H 1.203(6) 0.542(11) 0.7461(19) 0.042 Uiso 0.5 1 d R . P D -2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A N1A C8A 109.03(19) . . ?
N1A C8A C7A 130.1(2) . . ?
N1A C8A C9A 107.5(2) . . ?
C7A C8A C9A 122.4(2) . . ?
N1A C2A C10A 120.1(2) . . ?
C3A C2A N1A 109.7(2) . . ?
C3A C2A C10A 130.2(2) . . ?
C7A C6A C5A 121.4(2) . . ?
C6A C7A C8A 117.4(2) . . ?
C8A C9A C3A 106.67(19) . . ?
C4A C9A C8A 118.9(2) . . ?
C4A C9A C3A 134.4(2) . . ?
C2A C3A C9A 107.0(2) . . ?
C4A C5A C6A 121.0(2) . . ?
C5A C4A C9A 118.8(2) . . ?
C8 N1 C2 109.36(19) . . ?
N1 C8 C9 107.3(2) . . ?
N1 C8 C7 130.4(2) . . ?
C7 C8 C9 122.2(2) . . ?
C4 C5 C6 121.2(2) . . ?
C8 C9 C3 106.6(2) . . ?
C4 C9 C8 118.4(2) . . ?
C4 C9 C3 135.0(2) . . ?
C5 C4 C9 119.1(2) . . ?
C6 C7 C8 117.6(2) . . ?
C7 C6 C5 121.4(2) . . ?
N1 C2 C10 120.8(2) . . ?
C3 C2 N1 109.2(2) . . ?
C3 C2 C10 130.0(2) . . ?
O1A C10A C2A 110.2(2) . . ?
O1 C10 C2 111.58(19) . . ?
C2 C3 C9 107.6(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C10A 1.420(3) . ?
N1A C8A 1.378(3) . ?
N1A C2A 1.376(3) . ?
C8A C7A 1.393(3) . ?
C8A C9A 1.411(3) . ?
C2A C3A 1.362(3) . ?
C2A C10A 1.494(3) . ?
C6A C7A 1.384(3) . ?
C6A C5A 1.400(3) . ?
C9A C3A 1.438(3) . ?
C9A C4A 1.402(3) . ?
C5A C4A 1.389(3) . ?
N1 C8 1.373(3) . ?
N1 C2 1.382(3) . ?
C8 C9 1.419(3) . ?
C8 C7 1.396(3) . ?
C5 C4 1.380(3) . ?
C5 C6 1.399(3) . ?
C9 C4 1.410(3) . ?
C9 C3 1.431(3) . ?
C7 C6 1.381(3) . ?
C2 C10 1.486(3) . ?
C2 C3 1.363(3) . ?
O1 C10 1.434(3) . ?
