#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/00/2200081.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_2200081
loop_
_publ_author_name
'Lynch, Daniel E.'
'McClenaghan, Ian'
_publ_section_title
;
 2-Chloro-4-methylquinoline
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o54
_journal_page_last               o55
_journal_paper_doi               10.1107/S1600536800019590
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C10 H8 Cl N'
_chemical_formula_sum            'C10 H8 Cl N'
_chemical_formula_weight         177.62
_chemical_melting_point          330.0(10)
_chemical_name_systematic        2-Chloro-4-methylquinoline
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.721(3)
_cell_length_b                   7.8961(16)
_cell_length_c                   16.617(3)
_cell_measurement_reflns_used    3728
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1669.1(6)
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full .989
_diffrn_measured_fraction_theta_max .989
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0741
_diffrn_reflns_av_sigmaI/netI    .0576
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7671
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.93
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .392
_exptl_absorpt_correction_T_max  .973
_exptl_absorpt_correction_T_min  .926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          .20
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .07
_refine_diff_density_max         .33
_refine_diff_density_min         -.36
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          .060
_refine_ls_R_factor_gt           .043
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0699P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .115
_reflns_number_gt                1466
_reflns_number_total             1892
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6016.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '329-331 K' was changed to
'330.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '329-331 K' was changed to
'330.0(10)' - the average value was taken and precision was
estimated.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2200081
_cod_database_fobs_code          2200081
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 .65826(10) -.06443(14) .49091(8) .0262(3) Uani d . 1 . . N
C2 .75263(12) -.04143(18) .46408(11) .0263(4) Uani d . 1 . . C
Cl2 .76408(4) .05756(5) .37023(2) .03468(19) Uani d . 1 . . Cl
C3 .84655(13) -.08847(18) .50317(10) .0270(4) Uani d . 1 . . C
H3 .9128 -.0657 .4791 .034 Uiso calc R 1 . . H
C4 .84099(12) -.16720(17) .57612(9) .0255(4) Uani d . 1 . . C
C41 .93894(13) -.2178(2) .62011(10) .0327(4) Uani d . 1 . . C
H41 .9995 -.2074 .5840 .041 Uiso calc R 1 . . H
H42 .9325 -.3354 .6383 .041 Uiso calc R 1 . . H
H43 .9488 -.1436 .6668 .041 Uiso calc R 1 . . H
C5 .72124(13) -.27871(19) .68369(10) .0291(4) Uani d . 1 . . C
H5 .7796 -.3161 .7146 .036 Uiso calc R 1 . . H
C6 .62223(13) -.30384(19) .71223(10) .0328(4) Uani d . 1 . . C
H6 .6122 -.3583 .7626 .041 Uiso calc R 1 . . H
C7 .53455(13) -.24940(19) .66735(10) .0328(4) Uani d . 1 . . C
H7 .4657 -.2675 .6877 .041 Uiso calc R 1 . . H
C8 .54789(12) -.17088(17) .59497(11) .0293(4) Uani d . 1 . . C
H8 .4884 -.1343 .5651 .037 Uiso calc R 1 . . H
C9 .65001(12) -.14378(17) .56429(9) .0250(4) Uani d . 1 . . C
C10 .73904(11) -.19804(17) .60897(11) .0246(4) Uani d . 1 . . C
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 .0247(8) .0258(7) .0280(7) .0007(5) -.0037(6) -.0021(5)
C2 .0310(10) .0222(8) .0258(9) -.0001(5) -.0023(7) -.0035(6)
Cl2 .0395(3) .0365(3) .0280(3) -.00297(16) -.00131(17) .00304(15)
C3 .0223(9) .0276(7) .0310(8) -.0019(6) -.0008(7) -.0047(6)
C4 .0222(8) .0239(7) .0305(9) .0012(6) -.0038(7) -.0076(6)
C41 .0264(9) .0344(8) .0373(10) .0022(7) -.0072(7) -.0016(7)
C5 .0306(9) .0286(8) .0281(9) .0013(6) -.0046(7) -.0022(6)
C6 .0366(10) .0338(9) .0279(9) -.0007(7) .0007(8) -.0008(7)
C7 .0273(9) .0377(9) .0335(10) -.0023(7) .0037(7) -.0019(7)
C8 .0228(9) .0299(8) .0351(9) .0022(6) -.0032(7) -.0039(6)
C9 .0247(9) .0232(7) .0272(8) .0002(6) -.0021(7) -.0046(6)
C10 .0260(9) .0200(8) .0280(8) .0009(6) -.0050(6) -.0064(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .1585 '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
C2 N1 C9 116.14(13)
N1 C2 C3 126.21(15)
N1 C2 Cl2 116.56(12)
C3 C2 Cl2 117.23(12)
C4 C3 C2 119.05(14)
C4 C3 H3 120.5
C2 C3 H3 120.5
C3 C4 C10 117.68(14)
C3 C4 C41 120.78(14)
C10 C4 C41 121.54(14)
C4 C41 H41 109.5
C4 C41 H42 109.5
H41 C41 H42 109.5
C4 C41 H43 109.5
H41 C41 H43 109.5
H42 C41 H43 109.5
C6 C5 C10 121.34(15)
C6 C5 H5 119.3
C10 C5 H5 119.3
C5 C6 C7 120.27(16)
C5 C6 H6 119.9
C7 C6 H6 119.9
C8 C7 C6 120.46(15)
C8 C7 H7 119.8
C6 C7 H7 119.8
C7 C8 C9 120.12(14)
C7 C8 H8 119.9
C9 C8 H8 119.9
N1 C9 C8 117.36(13)
N1 C9 C10 122.70(14)
C8 C9 C10 119.95(15)
C5 C10 C9 117.86(14)
C5 C10 C4 123.92(14)
C9 C10 C4 118.22(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.293(2) ?
N1 C9 . 1.375(2) ?
C2 C3 . 1.410(2) ?
C2 Cl2 . 1.7504(18) ?
C3 C4 . 1.364(2) ?
C3 H3 . .95 ?
C4 C10 . 1.428(2) ?
C4 C41 . 1.499(2) ?
C41 H41 . .98 ?
C41 H42 . .98 ?
C41 H43 . .98 ?
C5 C6 . 1.360(2) ?
C5 C10 . 1.414(2) ?
C5 H5 . .95 ?
C6 C7 . 1.409(2) ?
C6 H6 . .95 ?
C7 C8 . 1.364(2) ?
C7 H7 . .95 ?
C8 C9 . 1.412(2) ?
C8 H8 . .95 ?
C9 C10 . 1.420(2) ?
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
_geom_hbond_publ_flag
C8 H8 N1 5_656 .95 2.61 3.517(2) 159.8 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C9 N1 C2 C3 -.6(2)
C9 N1 C2 Cl2 179.38(10)
N1 C2 C3 C4 .5(2)
Cl2 C2 C3 C4 -179.46(11)
C2 C3 C4 C10 .1(2)
C2 C3 C4 C41 -179.38(13)
C10 C5 C6 C7 .0(2)
C5 C6 C7 C8 -.1(2)
C6 C7 C8 C9 .1(2)
C2 N1 C9 C8 -179.87(13)
C2 N1 C9 C10 .1(2)
C7 C8 C9 N1 179.80(13)
C7 C8 C9 C10 -.1(2)
C6 C5 C10 C9 .0(2)
C6 C5 C10 C4 179.61(14)
N1 C9 C10 C5 -179.85(12)
C8 C9 C10 C5 .1(2)
N1 C9 C10 C4 .5(2)
C8 C9 C10 C4 -179.57(12)
C3 C4 C10 C5 179.80(13)
C41 C4 C10 C5 -.7(2)
C3 C4 C10 C9 -.6(2)
C41 C4 C10 C9 178.93(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 62656
