Crystal structures of five (2-chloroquinolin-3-yl)methyl ethers: supramolecular assembly in one and two dimensions mediated by hydrogen bonding and π–π stacking
Sowmya, Haliwana B. V.; Suresha Kumara, Tholappanavara H.; Gopalpur, Negendrappa; Jasinski, Jerry P.; Millikan, Sean P.; Yathirajan, Hemmige S.; Glidewell, Christopher; Acta Crystallographica Section E 71 (2015) 609–617; doi:10.1107/S2056989015008233

data_2240589
_publ_section_title
;
 Crystal structures of five (2-chloroquinolin-3-yl)methyl ethers:
 supramolecular assembly in one and two dimensions mediated by hydrogen
 bonding and \p--\p stacking
;
_journal_coeditor_code           SU5121
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              609
_journal_page_last               617
_journal_paper_doi               10.1107/S2056989015008233
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C20 H14 Cl N O'
_chemical_formula_moiety         'C20 H14 Cl N O'
_chemical_formula_sum            'C20 H14 Cl N O'
_chemical_formula_weight         319.77
_chemical_name_systematic
;
2-Chloro-3-[(naphthalen-1-yloxy)methyl]quinoline
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 98.527(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.3165(3)
_cell_length_b                   10.5098(4)
_cell_length_c                   13.6201(7)
_cell_measurement_reflns_used    2014
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.572
_cell_measurement_theta_min      3.281
_cell_volume                     752.62(6)
_computing_cell_refinement
;
CrysAlisPro (Agilent, 2012)
;
_computing_data_collection
;
CrysAlisPro (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlisRed (Agilent, 2012)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Agilent Eos Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_max       6
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_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4606
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.572
_diffrn_reflns_theta_min         3.281
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.265
_exptl_absorpt_correction_T_max  0.834
_exptl_absorpt_correction_T_min  0.551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
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_refine_diff_density_min         -0.194
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.007(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2014
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0579P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                1938
_reflns_number_total             2014
_reflns_threshold_expression     I>2\s(I)
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_cod_data_source_block           IV
_cod_database_code               2240589
_cod_database_fobs_code          2240589
_shelx_estimated_absorpt_t_min   0.513
_shelx_estimated_absorpt_t_max   0.840
_shelx_hkl_checksum              11473
_shelx_res_checksum              22202
_shelxl_version_number           2.014