#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/67/2236766.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2236766
loop_
_publ_author_name
'Ismail, Sharifah Shafiqah'
'Khaledi, Hamid'
'Mohd Ali, Hapipah'
_publ_section_title
;
 5-Methyl-1H-indole-3-carbaldehyde
;
_journal_coeditor_code           ZL2498
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2691
_journal_paper_doi               10.1107/S1600536812034873
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C10 H9 N O'
_chemical_formula_moiety         'C10 H9 N O'
_chemical_formula_sum            'C10 H9 N O'
_chemical_formula_weight         159.18
_chemical_name_systematic
;
5-Methyl-1H-indole-3-carbaldehyde
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.9456(19)
_cell_length_b                   5.7029(6)
_cell_length_c                   8.6333(9)
_cell_measurement_reflns_used    1172
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.06
_cell_measurement_theta_min      2.40
_cell_volume                     834.31(15)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5499
_diffrn_reflns_theta_full        28.75
_diffrn_reflns_theta_max         28.75
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_correction_T_min  0.9621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lath
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1147
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0596P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                717
_reflns_number_total             1147
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zl2498.cif
_cod_data_source_block           I
_cod_database_code               2236766
_cod_database_fobs_code          2236766
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.27204(11) 1.0610(3) 0.6573(2) 0.0742(6) Uani d . 1 1
N N1 0.29282(16) 0.4126(4) 0.3481(3) 0.0760(7) Uani d . 1 1
H H1N 0.2766(15) 0.285(5) 0.290(5) 0.091 Uiso d . 1 1
C C1 0.2435(2) 0.5303(4) 0.4384(3) 0.0717(8) Uani d . 1 1
H H1 0.1913 0.4879 0.4563 0.086 Uiso calc R 1 1
C C2 0.27969(14) 0.7233(4) 0.5018(3) 0.0587(6) Uani d . 1 1
C C3 0.35916(14) 0.7227(4) 0.4414(3) 0.0535(6) Uani d . 1 1
C C4 0.42432(15) 0.8710(4) 0.4561(3) 0.0554(6) Uani d . 1 1
H H4 0.4212 1.0036 0.5185 0.066 Uiso calc R 1 1
C C5 0.49316(16) 0.8208(4) 0.3782(3) 0.0638(7) Uani d . 1 1
C C6 0.49673(18) 0.6225(5) 0.2839(4) 0.0785(8) Uani d . 1 1
H H6 0.5434 0.5904 0.2311 0.094 Uiso calc R 1 1
C C7 0.4341(2) 0.4736(5) 0.2661(3) 0.0766(8) Uani d . 1 1
H H7 0.4377 0.3422 0.2026 0.092 Uiso calc R 1 1
C C8 0.36502(18) 0.5241(4) 0.3453(3) 0.0626(7) Uani d . 1 1
C C9 0.24192(16) 0.8851(4) 0.6026(3) 0.0640(6) Uani d . 1 1
H H9 0.1897 0.8544 0.6292 0.077 Uiso calc R 1 1
C C10 0.56347(18) 0.9773(6) 0.3966(4) 0.0860(10) Uani d . 1 1
H H10A 0.5654 1.0866 0.3121 0.129 Uiso calc R 1 1
H H10B 0.6107 0.8842 0.3969 0.129 Uiso calc R 1 1
H H10C 0.5595 1.0615 0.4926 0.129 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C1 N1 C8 109.7(2)
C1 N1 H1N 121.9(18)
C8 N1 H1N 128.1(18)
N1 C1 C2 111.0(3)
N1 C1 H1 124.5
C2 C1 H1 124.5
C1 C2 C9 124.3(3)
C1 C2 C3 105.7(2)
C9 C2 C3 130.0(2)
C4 C3 C8 119.0(2)
C4 C3 C2 134.7(2)
C8 C3 C2 106.3(2)
C5 C4 C3 120.0(2)
C5 C4 H4 120.0
C3 C4 H4 120.0
C4 C5 C6 119.4(3)
C4 C5 C10 119.9(2)
C6 C5 C10 120.7(3)
C7 C6 C5 122.3(3)
C7 C6 H6 118.8
C5 C6 H6 118.8
C6 C7 C8 118.1(2)
C6 C7 H7 121.0
C8 C7 H7 121.0
N1 C8 C7 131.4(2)
N1 C8 C3 107.3(2)
C7 C8 C3 121.2(3)
O1 C9 C2 125.6(3)
O1 C9 H9 117.2
C2 C9 H9 117.2
C5 C10 H10A 109.5
C5 C10 H10B 109.5
H10A C10 H10B 109.5
C5 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.221(3)
N1 C1 1.326(4)
N1 C8 1.379(4)
N1 H1N 0.93(3)
C1 C2 1.374(3)
C1 H1 0.9300
C2 C9 1.421(3)
C2 C3 1.444(3)
C3 C4 1.397(3)
C3 C8 1.408(3)
C4 C5 1.377(3)
C4 H4 0.9300
C5 C6 1.395(4)
C5 C10 1.497(4)
C6 C7 1.368(4)
C6 H6 0.9300
C7 C8 1.385(4)
C7 H7 0.9300
C9 H9 0.9300
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N O1 4_544 0.93(3) 1.90(3) 2.818(3) 169(3)
C9 H9 Cg 4_555 0.93 2.91 3.312(3) 107
loop_
_iucr_refine_instructions_details
;
TITL 1 in Pca2(1)
CELL 0.71073  16.9456   5.7029   8.6333  90.000  90.000  90.000
ZERR    4.00   0.0019   0.0006   0.0009   0.000   0.000   0.000
LATT -1
SYMM -X, -Y, 0.5+Z
SYMM 0.5+X, -Y, Z
SYMM 0.5-X, Y, 0.5+Z
SFAC C  H  N  O
UNIT 40 36  4  4
eqiv   $1 1/2-x,-1+y,-1/2+z
HTAB N1 O1_$1
mpla o1 n1 c1 c2 c3 c4 c5 c6 c7 c8 c9 c10
merg 3
L.S. 4
ACTA
BOND $H
SIZE 0.050 0.150 0.470
TEMP 23.000
WGHT    0.059600
FVAR       0.38343
O1    4    0.272045    1.060957    0.657298    11.00000    0.08431    0.06401 =
         0.07432   -0.01010    0.00856    0.01062
N1    3    0.292822    0.412560    0.348138    11.00000    0.10914    0.05650 =
         0.06224   -0.00533   -0.01463   -0.01291
H1N   2    0.276555    0.284942    0.289904    11.00000   -1.20000
C1    1    0.243455    0.530287    0.438355    11.00000    0.08205    0.06604 =
         0.06707    0.00808   -0.01095   -0.01429
AFIX  43
H1    2    0.191251    0.487929    0.456297    11.00000   -1.20000
AFIX   0
C2    1    0.279689    0.723259    0.501838    11.00000    0.07217    0.05326 =
         0.05076    0.00331   -0.00304   -0.00125
C3    1    0.359156    0.722689    0.441442    11.00000    0.06678    0.04986 =
         0.04400   -0.00128   -0.00704    0.00560
C4    1    0.424322    0.871015    0.456130    11.00000    0.06390    0.05278 =
         0.04953   -0.00028   -0.00520    0.00263
AFIX  43
H4    2    0.421203    1.003644    0.518508    11.00000   -1.20000
AFIX   0
C5    1    0.493165    0.820808    0.378241    11.00000    0.06400    0.06993 =
         0.05747    0.00733   -0.00221    0.01413
C6    1    0.496725    0.622493    0.283855    11.00000    0.08075    0.08689 =
         0.06784    0.00321    0.00744    0.02946
AFIX  43
H6    2    0.543351    0.590370    0.231145    11.00000   -1.20000
AFIX   0
C7    1    0.434052    0.473568    0.266077    11.00000    0.10514    0.06565 =
         0.05900   -0.01325    0.00079    0.02373
AFIX  43
H7    2    0.437699    0.342213    0.202642    11.00000   -1.20000
AFIX   0
C8    1    0.365021    0.524108    0.345292    11.00000    0.08879    0.04883 =
         0.05025   -0.00207   -0.01117    0.00508
C9    1    0.241915    0.885077    0.602604    11.00000    0.06621    0.06830 =
         0.05738    0.01243    0.00133    0.00831
AFIX  43
H9    2    0.189744    0.854356    0.629180    11.00000   -1.20000
AFIX   0
C10   1    0.563467    0.977292    0.396619    11.00000    0.06768    0.10199 =
         0.08841    0.01356    0.00322    0.00082
AFIX 137
H10A  2    0.565366    1.086619    0.312147    11.00000   -1.50000
H10B  2    0.610657    0.884153    0.396898    11.00000   -1.50000
H10C  2    0.559465    1.061459    0.492598    11.00000   -1.50000
HKLF 4
REM  1 in Pca2(1)
REM R1 =  0.0378 for    717 Fo > 4sig(Fo)  and  0.0735 for all   1147 data
REM    113 parameters refined using      1 restraints
END
WGHT      0.0590      0.0000
REM Highest difference peak  0.115,  deepest hole -0.143,  1-sigma level  0.032
Q1    1   0.5995  0.9066  0.2739  11.00000  0.05    0.11
Q2    1   0.6704  0.8348  0.5022  11.00000  0.05    0.10
Q3    1   0.3895  1.1080  0.6736  11.00000  0.05    0.10
Q4    1   0.1309  0.9192  0.6795  11.00000  0.05    0.10
;
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 227492
