#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/93/2019306.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_2019306
loop_
_publ_author_name
'Soave, Raffaella'
'Colombo, Pietro'
_publ_section_title
;
 Intermolecular C---H···O,
 Cl···Cl and π--π interactions in the
 2-dichloromethyl derivative of vitamin K₃
;
_journal_coeditor_code           KY3044
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1563
_journal_page_last               1566
_journal_paper_doi               10.1107/S010827011303196X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C12 H8 Cl2 O2'
_chemical_formula_moiety         'C12 H8 Cl2 O2'
_chemical_formula_sum            'C12 H8 Cl2 O2'
_chemical_formula_weight         255.08
_chemical_name_common
;
2-Dichloromethyl-3-methyl-1,4-naphthalenedione
;
_chemical_name_systematic
;
2-Dichloromethyl-3-methyl-1,4-dihydronaphthalene-1,4-dione
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.166(3)
_cell_length_b                   6.8812(14)
_cell_length_c                   11.958(2)
_cell_measurement_reflns_used    2767
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      43.10
_cell_measurement_theta_min      4.60
_cell_volume                     1083.4(4)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_collection       'SAINT-Plus (Bruker, 1999)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25336
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.991
_diffrn_reflns_theta_min         2.301
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.7853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.399
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0481
_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)+(0.0640P)²+0.9747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1612
_reflns_number_gt                908
_reflns_number_total             1703
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ky3044.cif
_cod_data_source_block           I
_cod_database_code               2019306
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           2.013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, 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_occupancy
Cl Cl1 0.12535(6) 0.03696(16) 0.54982(7) 0.0583(3) Uani d 1
O O1 0.2587(2) 0.2500 0.3787(2) 0.0568(10) Uani d 1
O O2 0.5444(2) 0.2500 0.6919(2) 0.0494(9) Uani d 1
C C1 0.3241(3) 0.2500 0.4500(3) 0.0342(9) Uani d 1
C C2 0.4332(3) 0.2500 0.4174(3) 0.0290(8) Uani d 1
C C3 0.4597(3) 0.2500 0.3052(3) 0.0363(10) Uani d 1
H H3 0.4094 0.2500 0.2506 0.044 Uiso calc 1
C C4 0.5603(3) 0.2500 0.2747(3) 0.0414(11) Uani d 1
H H4 0.5781 0.2500 0.1995 0.050 Uiso calc 1
C C5 0.6347(3) 0.2500 0.3557(4) 0.0406(10) Uani d 1
H H5 0.7027 0.2500 0.3345 0.049 Uiso calc 1
C C6 0.6098(3) 0.2500 0.4677(4) 0.0373(10) Uani d 1
H H6 0.6606 0.2500 0.5217 0.045 Uiso calc 1
C C7 0.5079(3) 0.2500 0.4996(3) 0.0288(9) Uani d 1
C C8 0.4798(3) 0.2500 0.6195(3) 0.0324(9) Uani d 1
C C9 0.3694(3) 0.2500 0.6506(3) 0.0306(9) Uani d 1
C C10 0.2983(3) 0.2500 0.5707(3) 0.0315(9) Uani d 1
C C11 0.3483(3) 0.2500 0.7744(3) 0.0439(11) Uani d 1
H H11A 0.4065 0.2993 0.8137 0.066 Uiso calc 0.5
H H11B 0.3345 0.1197 0.7988 0.066 Uiso calc 0.5
H H11C 0.2906 0.3309 0.7897 0.066 Uiso calc 0.5
C C12 0.1873(3) 0.2500 0.5999(3) 0.0417(11) Uani d 1
H H12 0.1819 0.2500 0.6816 0.063 Uiso calc 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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C10 . . 121.5(3) yes
O1 C1 C2 . . 120.1(3) yes
C10 C1 C2 . . 118.4(3) yes
C3 C2 C7 . . 120.4(3) no
C3 C2 C1 . . 119.8(3) no
C7 C2 C1 . . 119.9(3) yes
C4 C3 C2 . . 120.0(4) no
C4 C3 H3 . . 120.0 no
C2 C3 H3 . . 120.0 no
C3 C4 C5 . . 119.9(4) no
C3 C4 H4 . . 120.0 no
C5 C4 H4 . . 120.0 no
C4 C5 C6 . . 120.9(4) no
C4 C5 H5 . . 119.5 no
C6 C5 H5 . . 119.5 no
C5 C6 C7 . . 119.6(4) no
C5 C6 H6 . . 120.2 no
C7 C6 H6 . . 120.2 no
C2 C7 C6 . . 119.2(4) no
C2 C7 C8 . . 120.5(3) yes
C6 C7 C8 . . 120.4(3) no
O2 C8 C7 . . 121.0(3) yes
O2 C8 C9 . . 120.2(4) yes
C7 C8 C9 . . 118.8(3) yes
C10 C9 C8 . . 120.1(3) yes
C10 C9 C11 . . 124.9(3) no
C8 C9 C11 . . 115.0(3) no
C9 C10 C1 . . 122.3(3) yes
C9 C10 C12 . . 121.0(3) yes
C1 C10 C12 . . 116.7(3) yes
C9 C11 H11A . . 109.5 no
C9 C11 H11B . . 109.5 no
H11A C11 H11B . . 109.5 no
C9 C11 H11C . . 109.5 no
H11A C11 H11C . . 109.5 no
H11B C11 H11C . . 109.5 no
C10 C12 Cl1 . . 111.52(16) no
C10 C12 Cl1 . 7_565 111.52(16) no
Cl1 C12 Cl1 . 7_565 110.8(2) no
C10 C12 H12 . . 107.6 no
Cl1 C12 H12 . . 107.6 no
Cl1 C12 H12 7_565 . 107.6 no
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
Cl1 C12 . 1.781(2) yes
O1 C1 . 1.212(4) yes
O2 C8 . 1.214(4) yes
C1 C10 . 1.483(5) yes
C1 C2 . 1.487(5) yes
C2 C3 . 1.386(5) yes
C2 C7 . 1.391(5) yes
C3 C4 . 1.374(5) yes
C3 H3 . 0.9300 no
C4 C5 . 1.378(6) yes
C4 H4 . 0.9300 no
C5 C6 . 1.379(6) yes
C5 H5 . 0.9300 no
C6 C7 . 1.394(5) yes
C6 H6 . 0.9300 no
C7 C8 . 1.482(5) yes
C8 C9 . 1.499(5) yes
C9 C10 . 1.338(5) yes
C9 C11 . 1.507(5) yes
C10 C12 . 1.504(5) yes
C11 H11A . 0.9600 no
C11 H11B . 0.9600 no
C11 H11C . 0.9600 no
C12 Cl1 7_565 1.781(2) no
C12 H12 . 0.9800 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 Cl1 3.5460(10) 5_556 yes
Cl1 O1 3.0690(10) . yes
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
C12 H12 O2 4_456 0.98 2.36 3.120(5) 134.0
C5 H5 O1 4_555 0.93 2.65 3.243(5) 121.9
C4 H4 O1 4_555 0.93 2.55 3.192(5) 126.1
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_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . 0.0000(10) no
C10 C1 C2 C3 . 180.0000(10) no
O1 C1 C2 C7 . 180.0000(10) no
C10 C1 C2 C7 . 0.0000(10) no
C7 C2 C3 C4 . 0.0000(10) no
C1 C2 C3 C4 . 180.000000 no
C2 C3 C4 C5 . 0.0000(10) no
C3 C4 C5 C6 . 0.0000(10) no
C4 C5 C6 C7 . 0.0000(10) no
C3 C2 C7 C6 . 0.0000(10) no
C1 C2 C7 C6 . 180.0000(10) no
C3 C2 C7 C8 . 180.0000(10) no
C1 C2 C7 C8 . 0.0000(10) no
C5 C6 C7 C2 . 0.0000(10) no
C5 C6 C7 C8 . 180.0000(10) no
C2 C7 C8 O2 . 180.0000(10) no
C6 C7 C8 O2 . 0.0000(10) no
C2 C7 C8 C9 . 0.0000(10) no
C6 C7 C8 C9 . 180.0000(10) no
O2 C8 C9 C10 . 180.0000(10) no
C7 C8 C9 C10 . 0.0000(10) no
O2 C8 C9 C11 . 0.0000(10) no
C7 C8 C9 C11 . 180.0000(10) no
C8 C9 C10 C1 . 0.0000(10) no
C11 C9 C10 C1 . 180.0000(10) no
C8 C9 C10 C12 . 180.0000(10) no
C11 C9 C10 C12 . 0.0000(10) no
O1 C1 C10 C9 . 180.0000(10) no
C2 C1 C10 C9 . 0.0000(10) no
O1 C1 C10 C12 . 0.0000(10) no
C2 C1 C10 C12 . 180.0000(10) no
C9 C10 C12 Cl1 . -117.78(18) no
C1 C10 C12 Cl1 . 62.22(18) no
C9 C10 C12 Cl1 7_565 117.78(18) no
C1 C10 C12 Cl1 7_565 -62.22(18) no
