Supramolecular Assemblies of 2-hydroxy-3-naphthoic Acid and N-Heterocycles via Various Strong Hydrogen Bonds and Weak X•••π (X= C–H, π) Interactions
Pan, Yanyan; Xing, Peiqi; Geng, Xiujuan; Zhu, Yujing; Liu, Faqian; Wang, Lei; RSC Adv.  (2015) –; doi:10.1039/C5RA03837E

data_7220077
_publ_section_title
;
 Supramolecular Assemblies of 2-hydroxy-3-naphthoic Acid and
 N-Heterocycles via Various Strong Hydrogen Bonds and Weak
 X&#x2022;&#x2022;&#x2022;\p (X= C--H, \p) Interactions
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA03837E
_journal_year                    2015
_chemical_formula_moiety         'C10 H15 N2, C11 H7 O3'
_chemical_formula_sum            'C21 H22 N2 O3'
_chemical_formula_weight         350.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-02-07
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2014-11-04 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2836(6)
_cell_length_b                   8.1666(10)
_cell_length_c                   34.870(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1789.4(3)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            5111
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.336
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 657 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -2.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0450P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1138
_reflns_Friedel_coverage         0.593
_reflns_Friedel_fraction_full    0.838
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                2211
_reflns_number_total             2979
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra03837e2.cif
_cod_data_source_block           4
_cod_database_code               7220077
_shelxl_version_number           2013-2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C6(H6A,H6B), C9(H9A,H9B), C11(H11A,H11B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              25796