#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:36:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180400 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/69/7206934.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_7206934
loop_
_publ_author_name
'Hazra, Dipak K.'
'Mukherjee, Alok K.'
'Helliwell, Madeleine'
'Mukherjee, Monika'
_publ_section_title
;
 Topological features and electronic structure of
 4-chloro-1H-pyrrolo[2,3-b]pyridine: experimental charge density analysis
 and DFT studies
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              993
_journal_paper_doi               10.1039/c1ce05615h
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C7 H5 Cl N2'
_chemical_formula_weight         152.58
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 90.500(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2586(2)
_cell_length_b                   8.9160(3)
_cell_length_c                   13.8165(5)
_cell_measurement_reflns_used    956
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      49.36
_cell_measurement_theta_min      2.72
_cell_volume                     647.77(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6767
_diffrn_reflns_theta_full        50.31
_diffrn_reflns_theta_max         50.31
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    0.495
_exptl_absorpt_correction_T_max  0.9295
_exptl_absorpt_correction_T_min  0.8057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.802
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.273
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         6767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.273
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0543
_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)+(0.0519P)²+0.1317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1297
_reflns_number_gt                6097
_reflns_number_total             6767
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05615h.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7206934
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
Cl1 Cl 0.15230(3) 0.407267(19) 0.361088(13) 0.01690(4) Uani 1 1 d
N1 N 0.87800(11) 0.05427(7) 0.38009(4) 0.01436(8) Uani 1 1 d
H1N H 0.999(4) -0.006(2) 0.4019(15) 0.044(5) Uiso 1 1 d
N2 N 0.73064(11) 0.13488(7) 0.53585(4) 0.01446(8) Uani 1 1 d
C1 C 0.80633(14) 0.08017(8) 0.28556(5) 0.01592(10) Uani 1 1 d
H1 H 0.893(3) 0.0308(18) 0.2319(11) 0.020(3) Uiso 1 1 d
C2 C 0.60393(13) 0.17752(8) 0.28110(5) 0.01523(9) Uani 1 1 d
H2 H 0.515(3) 0.2116(18) 0.2241(12) 0.021(3) Uiso 1 1 d
C3 C 0.54550(12) 0.21375(7) 0.37915(4) 0.01264(8) Uani 1 1 d
C4 C 0.72081(11) 0.13411(7) 0.43901(4) 0.01246(8) Uani 1 1 d
H6 H 0.251(3) 0.367(2) 0.5645(12) 0.023(4) Uiso 1 1 d
C5 C 0.55419(14) 0.22040(8) 0.57823(5) 0.01634(10) Uani 1 1 d
C6 C 0.37225(13) 0.30590(8) 0.52780(5) 0.01612(10) Uani 1 1 d
H5 H 0.566(4) 0.218(2) 0.6408(14) 0.030(4) Uiso 1 1 d
C7 C 0.36934(12) 0.30245(7) 0.42743(5) 0.01351(8) Uani 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.01400(6) 0.01591(7) 0.02073(7) 0.00203(5) -0.00255(5) 0.00300(4)
N1 0.01500(19) 0.01438(18) 0.01372(18) 0.00063(15) 0.00046(14) 0.00286(14)
N2 0.01417(18) 0.01577(19) 0.01342(17) 0.00060(15) 0.00001(14) 0.00192(14)
C1 0.0182(2) 0.0159(2) 0.0137(2) -0.00052(17) 0.00006(17) 0.00211(17)
C2 0.0173(2) 0.0152(2) 0.0132(2) -0.00033(17) -0.00133(16) 0.00116(17)
C3 0.01222(19) 0.01226(18) 0.01342(19) 0.00046(15) -0.00096(14) 0.00029(14)
C4 0.01180(18) 0.01216(18) 0.01343(19) 0.00077(15) -0.00036(14) 0.00075(14)
C5 0.0164(2) 0.0188(2) 0.0138(2) 0.00001(18) 0.00100(16) 0.00279(18)
C6 0.0151(2) 0.0177(2) 0.0156(2) -0.00043(18) 0.00146(17) 0.00276(17)
C7 0.01205(19) 0.01275(19) 0.0157(2) 0.00095(16) -0.00077(15) 0.00065(14)
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'
Cl Cl 0.1484 0.1585 '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
C4 N1 C1 108.43(5)
C4 N1 H1N 123.4(14)
C1 N1 H1N 128.1(14)
C4 N2 C5 114.77(6)
C2 C1 N1 110.75(6)
C2 C1 H1 128.0(9)
N1 C1 H1 121.2(9)
C1 C2 C3 105.85(6)
C1 C2 H2 127.3(10)
C3 C2 H2 126.8(10)
C7 C3 C4 115.80(6)
C7 C3 C2 137.06(6)
C4 C3 C2 107.14(5)
N2 C4 N1 125.47(6)
N2 C4 C3 126.70(6)
N1 C4 C3 107.83(5)
N2 C5 C6 124.32(6)
N2 C5 H5 112.3(12)
C6 C5 H5 123.4(12)
C7 C6 C5 119.07(6)
C7 C6 H6 121.8(10)
C5 C6 H6 119.1(10)
C6 C7 C3 119.34(6)
C6 C7 Cl1 121.25(5)
C3 C7 Cl1 119.41(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C7 1.7315(6)
N1 C4 1.3654(8)
N1 C1 1.3758(9)
N1 H1N 0.88(2)
N2 C4 1.3386(8)
N2 C5 1.3397(9)
C1 C2 1.3743(10)
C1 H1 0.979(15)
C2 C3 1.4287(9)
C2 H2 0.961(16)
C3 C7 1.3927(9)
C3 C4 1.4230(9)
C5 C6 1.4037(10)
C5 H5 0.867(19)
C6 C7 1.3869(10)
C6 H6 0.981(17)
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
C4 N1 C1 C2 0.46(8)
N1 C1 C2 C3 -0.29(8)
C1 C2 C3 C7 -179.88(8)
C1 C2 C3 C4 0.03(7)
C5 N2 C4 N1 -179.11(7)
C5 N2 C4 C3 0.13(10)
C1 N1 C4 N2 178.93(7)
C1 N1 C4 C3 -0.43(7)
C7 C3 C4 N2 0.82(10)
C2 C3 C4 N2 -179.10(7)
C7 C3 C4 N1 -179.82(6)
C2 C3 C4 N1 0.25(7)
C4 N2 C5 C6 -0.89(11)
N2 C5 C6 C7 0.65(12)
C5 C6 C7 C3 0.40(10)
C5 C6 C7 Cl1 -179.17(6)
C4 C3 C7 C6 -1.04(9)
C2 C3 C7 C6 178.86(8)
C4 C3 C7 Cl1 178.54(5)
C2 C3 C7 Cl1 -1.57(11)
