#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/24/8102441.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_8102441
loop_
_publ_author_name
'Tao Zeng'
'Kai-Jing Li'
'Yong Li'
_publ_section_title
;
 Crystal structure of
 2,6-dichloro-1,7,7-trimethyl-bicyclo[2.2.1]heptane, C10H16Cl2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              393
_journal_volume                  224
_journal_year                    2009
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C10 H16 Cl2'
_chemical_formula_sum            'C10 H16 Cl2'
_chemical_formula_weight         207.13
_chemical_name_systematic
;
2,6-dichloro-1,7,7-trimethylbicyclo[2.2.1]heptane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_cell_angle_alpha                90
_cell_angle_beta                 90.228(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6321(1)
_cell_length_b                   11.1976(2)
_cell_length_c                   12.5129(2)
_cell_measurement_reflns_used    1507
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.590
_cell_measurement_theta_min      2.44
_cell_volume                     1069.36(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Burker, 2002)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Burker, 2000)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.611
_diffrn_measured_fraction_theta_max 0.611
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD '
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5439
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.554
_exptl_absorpt_correction_T_max  0.809
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0510
_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)+(0.1022P)²]         where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1573
_reflns_number_gt                1159
_reflns_number_total             1507
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            1267-2607.cff
_cod_data_source_block           96
_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_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8102441
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl Uani 0.08683(11) 0.76738(8) 0.76887(8) 1.000 0.0745(3) . .
Cl2 Cl Uani 0.17655(12) 0.92406(7) 0.56157(8) 1.000 0.0716(3) . .
C1 C Uani 0.7035(5) 0.7205(3) 0.5615(3) 1.000 0.0662(11) . .
C2 C Uani 0.5826(3) 0.71408(19) 0.6596(2) 1.000 0.0422(7) . .
C3 C Uani 0.6349(5) 0.5995(3) 0.7195(3) 1.000 0.0671(10) . .
C4 C Uani 0.5857(3) 0.8281(2) 0.7292(2) 1.000 0.0472(8) . .
C5 C Uani 0.3804(3) 0.72484(18) 0.6335(2) 1.000 0.0402(7) . .
C6 C Uani 0.4442(4) 0.8005(3) 0.8121(2) 1.000 0.0601(10) . .
C7 C Uani 0.3122(3) 0.7253(2) 0.7487(2) 1.000 0.0487(8) . .
C8 C Uani 0.5114(4) 0.9219(2) 0.6526(3) 1.000 0.0596(9) . .
C9 C Uani 0.3841(4) 0.8500(2) 0.5825(2) 1.000 0.0471(7) . .
C10 C Uani 0.2990(5) 0.6306(3) 0.5623(3) 1.000 0.0701(11) . .
H1A H Uiso 0.82360 0.71740 0.58450 1.000 0.0990 calc R
H1B H Uiso 0.68280 0.79390 0.52380 1.000 0.0990 calc R
H1C H Uiso 0.67950 0.65430 0.51500 1.000 0.0990 calc R
H2 H Uiso 0.312(7) 0.635(4) 0.774(3) 1.000 0.076(11) . .
H3 H Uiso 0.610(7) 0.943(3) 0.616(4) 1.000 0.079(12) . .
H3A H Uiso 0.61200 0.53150 0.67500 1.000 0.1010 calc R
H3B H Uiso 0.56790 0.59320 0.78400 1.000 0.1010 calc R
H3C H Uiso 0.75750 0.60240 0.73690 1.000 0.1010 calc R
H4 H Uiso 0.427(4) 0.845(2) 0.513(3) 1.000 0.042(7) . .
H10A H Uiso 0.32780 0.55280 0.58930 1.000 0.1050 calc R
H10B H Uiso 0.34370 0.63890 0.49110 1.000 0.1050 calc R
H10C H Uiso 0.17410 0.64040 0.56130 1.000 0.1050 calc R
H11 H Uiso 0.431(7) 0.990(4) 0.684(4) 1.000 0.093(14) . .
H20 H Uiso 0.391(7) 0.873(4) 0.832(4) 1.000 0.087(12) . .
H24 H Uiso 0.490(11) 0.755(4) 0.885(6) 1.000 0.113(17) . .
H30 H Uiso 0.714(4) 0.842(2) 0.761(2) 1.000 0.042(7) . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 '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'
C C 0.0033 0.0016 '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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C2 C3 105.8(2) . . . no
C1 C2 C4 113.7(2) . . . no
C1 C2 C5 114.8(2) . . . no
C3 C2 C4 114.3(2) . . . no
C3 C2 C5 114.6(2) . . . no
C4 C2 C5 93.80(17) . . . no
C2 C4 C6 101.9(2) . . . no
C2 C4 C8 102.1(2) . . . no
C6 C4 C8 107.6(2) . . . no
C2 C5 C7 98.09(18) . . . no
C2 C5 C9 97.79(18) . . . no
C2 C5 C10 117.8(2) . . . no
C7 C5 C9 113.14(18) . . . no
C7 C5 C10 114.6(2) . . . no
C9 C5 C10 113.5(2) . . . no
C4 C6 C7 103.0(2) . . . no
Cl1 C7 C5 117.38(17) . . . yes
Cl1 C7 C6 114.19(18) . . . yes
C5 C7 C6 105.28(19) . . . no
C4 C8 C9 103.31(18) . . . no
Cl2 C9 C5 117.41(19) . . . yes
Cl2 C9 C8 113.26(17) . . . yes
C5 C9 C8 104.7(2) . . . no
C2 C1 H1A 109.00 . . . no
C2 C1 H1B 109.00 . . . no
C2 C1 H1C 109.00 . . . no
H1A C1 H1B 109.00 . . . no
H1A C1 H1C 109.00 . . . no
H1B C1 H1C 109.00 . . . no
C2 C3 H3A 109.00 . . . no
C2 C3 H3B 109.00 . . . no
C2 C3 H3C 109.00 . . . no
H3A C3 H3B 109.00 . . . no
H3A C3 H3C 109.00 . . . no
H3B C3 H3C 109.00 . . . no
C2 C4 H30 110.0(13) . . . no
C6 C4 H30 115.2(14) . . . no
C8 C4 H30 118.1(13) . . . no
C4 C6 H20 108(3) . . . no
C4 C6 H24 116(4) . . . no
C7 C6 H20 109(3) . . . no
C7 C6 H24 112(3) . . . no
H20 C6 H24 108(4) . . . no
Cl1 C7 H2 102(3) . . . no
C5 C7 H2 106(2) . . . no
C6 C7 H2 112(3) . . . no
C4 C8 H3 101(3) . . . no
C4 C8 H11 119(3) . . . no
C9 C8 H3 112(3) . . . no
C9 C8 H11 103(3) . . . no
H3 C8 H11 119(3) . . . no
Cl2 C9 H4 101.7(19) . . . no
C5 C9 H4 109.8(14) . . . no
C8 C9 H4 109.9(18) . . . no
C5 C10 H10A 109.00 . . . no
C5 C10 H10B 109.00 . . . no
C5 C10 H10C 109.00 . . . no
H10A C10 H10B 109.00 . . . no
H10A C10 H10C 110.00 . . . no
H10B C10 H10C 109.00 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.802(2) . . yes
Cl2 C9 1.806(3) . . yes
C1 C2 1.540(4) . . no
C2 C3 1.538(4) . . no
C2 C4 1.546(3) . . no
C2 C5 1.581(3) . . no
C4 C6 1.532(4) . . no
C4 C8 1.529(4) . . no
C5 C7 1.535(4) . . no
C5 C9 1.540(3) . . no
C5 C10 1.513(4) . . no
C6 C7 1.532(4) . . no
C8 C9 1.535(4) . . no
C1 H1A 0.9600 . . no
C1 H1B 0.9600 . . no
C1 H1C 0.9600 . . no
C3 H3A 0.9600 . . no
C3 H3B 0.9600 . . no
C3 H3C 0.9600 . . no
C4 H30 1.07(3) . . no
C6 H20 0.94(5) . . no
C6 H24 1.10(7) . . no
C7 H2 1.06(4) . . no
C8 H3 0.91(5) . . no
C8 H11 1.06(5) . . no
C9 H4 0.93(4) . . no
C10 H10A 0.9600 . . no
C10 H10B 0.9600 . . no
C10 H10C 0.9600 . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 Cl2 3.2077(13) . . no
Cl2 Cl2 3.5350(13) . 3_576 no
Cl2 Cl1 3.2077(13) . . no
Cl1 H10C 3.0400 . . no
Cl1 H1A 3.1000 . 1_455 no
Cl1 H3C 3.1400 . 1_455 no
Cl1 H30 2.97(3) . 1_455 no
Cl2 H2 3.13(4) . 2_556 no
Cl2 H3 3.14(5) . 3_676 no
C1 H3 2.68(4) . . no
C1 H4 2.60(3) . . no
C1 H10B 3.0200 . . no
C3 H2 2.59(5) . . no
C3 H10A 2.9000 . . no
C3 H24 2.93(7) . . no
C6 H3B 2.5300 . . no
C7 H3B 2.4900 . . no
C8 H1B 2.5300 . . no
C8 H3C 3.0100 . 2_656 no
C9 H1B 2.4800 . . no
C10 H1C 2.9800 . . no
C10 H3A 2.9800 . . no
H1A Cl1 3.1000 . 1_655 no
H1A H3C 2.3600 . . no
H1B C8 2.5300 . . no
H1B C9 2.4800 . . no
H1B H3 2.1100 . . no
H1B H4 2.0400 . . no
H1C C10 2.9800 . . no
H1C H3A 2.4800 . . no
H1C H10B 2.5800 . . no
H2 C3 2.59(5) . . no
H2 H3B 2.0100 . . no
H2 H10A 2.4900 . . no
H2 Cl2 3.13(4) . 2_546 no
H2 H11 2.52(7) . 2_546 no
H3 C1 2.68(4) . . no
H3 H1B 2.1100 . . no
H3 Cl2 3.14(5) . 3_676 no
H3A C10 2.9800 . . no
H3A H1C 2.4800 . . no
H3A H10A 2.4300 . . no
H3B C6 2.5300 . . no
H3B C7 2.4900 . . no
H3B H2 2.0100 . . no
H3B H24 2.2900 . . no
H3C Cl1 3.1400 . 1_655 no
H3C H1A 2.3600 . . no
H3C C8 3.0100 . 2_646 no
H4 C1 2.60(3) . . no
H4 H1B 2.0400 . . no
H4 H10B 2.4100 . . no
H10A C3 2.9000 . . no
H10A H2 2.4900 . . no
H10A H3A 2.4300 . . no
H10B C1 3.0200 . . no
H10B H1C 2.5800 . . no
H10B H4 2.4100 . . no
H10C Cl1 3.0400 . . no
H11 H20 2.29(7) . . no
H11 H2 2.52(7) . 2_556 no
H20 H11 2.29(7) . . no
H24 C3 2.93(7) . . no
H24 H3B 2.2900 . . no
H30 Cl1 2.97(3) . 1_655 no
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C4 C6 175.0(2) . . . . no
C1 C2 C4 C8 63.9(3) . . . . no
C3 C2 C4 C6 -63.3(3) . . . . no
C3 C2 C4 C8 -174.5(2) . . . . no
C5 C2 C4 C6 55.8(2) . . . . no
C5 C2 C4 C8 -55.3(2) . . . . no
C1 C2 C5 C7 -175.4(2) . . . . no
C1 C2 C5 C9 -60.6(2) . . . . no
C1 C2 C5 C10 61.2(3) . . . . no
C3 C2 C5 C7 61.8(2) . . . . no
C3 C2 C5 C9 176.7(2) . . . . no
C3 C2 C5 C10 -61.5(3) . . . . no
C4 C2 C5 C7 -57.08(18) . . . . no
C4 C2 C5 C9 57.8(2) . . . . no
C4 C2 C5 C10 179.6(2) . . . . no
C2 C4 C6 C7 -32.9(2) . . . . no
C8 C4 C6 C7 74.0(3) . . . . no
C2 C4 C8 C9 31.4(3) . . . . no
C6 C4 C8 C9 -75.3(3) . . . . no
C2 C5 C7 Cl1 167.37(15) . . . . no
C2 C5 C7 C6 39.1(2) . . . . no
C9 C5 C7 Cl1 65.3(2) . . . . no
C9 C5 C7 C6 -63.0(3) . . . . no
C10 C5 C7 Cl1 -67.0(3) . . . . no
C10 C5 C7 C6 164.7(2) . . . . no
C2 C5 C9 Cl2 -167.15(17) . . . . no
C2 C5 C9 C8 -40.6(2) . . . . no
C7 C5 C9 Cl2 -64.9(2) . . . . no
C7 C5 C9 C8 61.7(3) . . . . no
C10 C5 C9 Cl2 67.9(3) . . . . no
C10 C5 C9 C8 -165.6(2) . . . . no
C4 C6 C7 Cl1 -134.77(19) . . . . no
C4 C6 C7 C5 -4.6(3) . . . . no
C4 C8 C9 Cl2 135.53(19) . . . . no
C4 C8 C9 C5 6.5(3) . . . . no
