Intermolecular C—H···O, Cl···Cl and π‒π interactions in the 2-dichloromethyl derivative of vitamin K~3~
Soave, Raffaella; Colombo, Pietro; Acta Crystallographica Section C 69 (2013) 1563–1566; doi:10.1107/S010827011303196X

data_2019306
_publ_section_title
;
 Intermolecular C---H&#x00B7;&#x00B7;&#x00B7;O,
 Cl&#x00B7;&#x00B7;&#x00B7;Cl and \p--\p interactions in the
 2-dichloromethyl derivative of vitamin K~3~
;
_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       '\w 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/[\s^2^(Fo^2^)+(0.0640P)^2^+0.9747P] where P=(Fo^2^+2Fc^2^)/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>2\s(I)
_cod_data_source_file            ky3044.cif
_cod_data_source_block           I
_cod_database_code               2019306
_shelx_hkl_checksum              13896
_shelx_res_checksum              41152
_shelxl_version_number           2.013