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_2240587
_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          'C19 H15 Br Cl N O3'
_chemical_formula_moiety         'C19 H15 Br Cl N O3'
_chemical_formula_sum            'C19 H15 Br Cl N O3'
_chemical_formula_weight         420.67
_chemical_name_systematic
;
Methyl 5-bromo-2-[(2-chloro-6-methylquinolin-3-yl)methoxy]benzoate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.1920(3)
_cell_length_b                   11.98641(19)
_cell_length_c                   19.0307(3)
_cell_measurement_reflns_used    3421
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.449
_cell_measurement_theta_min      4.647
_cell_volume                     3465.44(10)
_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 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0554
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21861
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.449
_diffrn_reflns_theta_min         4.647
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.812
_exptl_absorpt_correction_T_max  0.680
_exptl_absorpt_correction_T_min  0.399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.488
_refine_ls_extinction_coef       0.00048(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0523P)^2^+1.8465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0933
_reflns_number_gt                3062
_reflns_number_total             3421
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            su5121sup1.cif
_cod_data_source_block           II
_cod_database_code               2240587
_cod_database_fobs_code          2240587
_shelx_estimated_absorpt_t_min   0.391
_shelx_estimated_absorpt_t_max   0.699
_shelx_hkl_checksum              37689
_shelx_res_checksum              68288
_shelxl_version_number           2.014