Continuous niobium phosphate catalysed Skraup reaction for quinoline synthesis from solketal
Jin, Jing; Guidi, Sandro; Abada, Zahra; Amara, Zacharias; Selva, Maurizio; George, Michael W.; Poliakoff, Martyn; Green Chem.  (2017) –; doi:10.1039/C6GC03140D

data_7228158
_publ_section_title
;
 Continuous niobium phosphate catalysed Skraup reaction for quinoline
 synthesis from solketal
;
_journal_name_full               'Green Chem.'
_journal_paper_doi               10.1039/C6GC03140D
_journal_year                    2017
_chemical_formula_moiety         'C16 H14 N2'
_chemical_formula_sum            'C16 H14 N2'
_chemical_formula_weight         234.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-02-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-11-14 deposited with the CCDC.
2017-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.794(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0024(9)
_cell_length_b                   6.9487(7)
_cell_length_c                   17.5896(15)
_cell_measurement_reflns_used    2492
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.5910
_cell_measurement_theta_min      5.0890
_cell_volume                     1208.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41n (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41n (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41n (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -38.00  28.00   2.00    2.00    --  -38.50  38.00 120.00   33
  2  \w    -19.00  67.00   2.00    2.00    --   43.08 -57.00 -30.00   43
  3  \w     32.00  68.00   2.00    2.00    --   43.08 -57.00-150.00   18
  4  \w     34.00  88.00   2.00    6.00    --  104.50 -45.00   0.00   27
  5  \w     82.00 130.00   2.00    6.00    --  104.50 -61.00 -90.00   24
  6  \w     50.00 172.00   2.00    6.00    --  104.50   0.00  90.00   61
  7  \w     39.00 119.00   2.00    6.00    --  104.50-125.00 150.00   40
  8  \w     24.00 106.00   2.00    6.00    --  104.50 -94.00 -60.00   41
  9  \w     35.00  83.00   2.00    6.00    --  104.50 -45.00-180.00   24
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0385956000
_diffrn_orient_matrix_UB_12      -0.2097684000
_diffrn_orient_matrix_UB_13      0.0150218000
_diffrn_orient_matrix_UB_21      0.1440908000
_diffrn_orient_matrix_UB_22      -0.0654945000
_diffrn_orient_matrix_UB_23      -0.0086421000
_diffrn_orient_matrix_UB_31      0.0450937000
_diffrn_orient_matrix_UB_32      0.0292229000
_diffrn_orient_matrix_UB_33      0.0869119000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4597
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.546
_diffrn_reflns_theta_min         5.089
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.594
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41n (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.164
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0567P)^2^+0.3196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2070
_reflns_number_total             2356
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6gc03140d2.cif
_cod_data_source_block           sgmpaa
_cod_database_code               7228158
_nottingham_internal_coll_name   SGMPAA
_nottingham_internal_coll_number 15114
_nottingham_internal_coll_client SG/MP
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '2.00, 6.00'
_nottingham_internal_coll_frame_width 2.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   03/09/2015
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_process_date 26/01/2016
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 1/2/2016
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 1/2/2016
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 1/2/2016
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 1/2/2016
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C16 H14 N2'
_chemical_oxdiff_usercomment
'SGMPAA #15114 GVB-720 IN FOMBLIN FIML ON A MICROMOUNT FOR SG/MP'
_reflns_odcompleteness_completeness 99.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C8(H8), C9(H9), C13(H13), C14(H14), C16(H16),
 C17(H17)
;
_shelx_res_checksum              5091
_shelx_hkl_checksum              26476
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.300
_oxdiff_exptl_absorpt_empirical_full_min 0.834