#------------------------------------------------------------------------------
#$Date: 2017-12-10 04:32:44 +0200 (Sun, 10 Dec 2017) $
#$Revision: 204128 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/05/1520575.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1520575
loop_
_publ_author_name
'Castillo, Juan-Carlos'
'Quiroga, Jairo'
'Abonia, Rodrigo'
'Rodriguez, Jean'
'Coquerel, Yoann'
_publ_section_title
;
 The Aryne aza-Diels-Alder Reaction: Flexible Syntheses of Isoquinolines.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3374
_journal_page_last               3377
_journal_paper_doi               10.1021/acs.orglett.5b01704
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C16 H15 N3'
_chemical_formula_sum            'C16 H15 N3'
_chemical_formula_weight         249.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date
;
'Thu Jul 24 15:47:01 2014'
;
_audit_creation_method
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_cell_angle_alpha                90.0
_cell_angle_beta                 98.985(2)
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   9.7773(2)
_cell_length_b                   6.90436(13)
_cell_length_c                   9.79548(19)
_cell_measurement_reflns_used    3198
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4260
_cell_measurement_theta_min      5.9370
_cell_volume                     653.14(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega  -34.00    9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0146  -57.0000 -120.0000 43

  2 omega   12.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0146  -57.0000 -120.0000 58

  3 omega   10.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0146  -99.0000 -150.0000 62

  4 omega   49.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -30.0000 -120.0000 42

  5 omega   37.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -45.0000    0.0000 61

  6 omega  115.00  141.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -77.0000   60.0000 26

  7 omega   83.00  175.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719   30.0000   60.0000 92

  8 omega  111.00  175.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  125.0000    0.0000 64

  9 omega   88.00  159.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719   45.0000  120.0000 71

 10 omega   56.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -94.0000    0.0000 53

 11 omega   57.00   83.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -77.0000   60.0000 26

 12 omega   48.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -30.0000   60.0000 43

 13 omega   42.00   68.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -45.0000  150.0000 26

 14 omega   30.00   87.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -30.0000  120.0000 57

 15 omega   52.00  112.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719 -105.0000  151.0000 60

 16 omega   25.00   96.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -94.0000  -60.0000 71

 17 omega   31.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -30.0000  -60.0000 38

 18 omega  -48.00   36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146   38.0000  150.0000 84

 19 omega -114.00  -15.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146  -57.0000    0.0000 99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1324819000
_diffrn_orient_matrix_UB_12      -0.0665997000
_diffrn_orient_matrix_UB_13      -0.0532972000
_diffrn_orient_matrix_UB_21      -0.0773765000
_diffrn_orient_matrix_UB_22      0.0061998000
_diffrn_orient_matrix_UB_23      -0.1495529000
_diffrn_orient_matrix_UB_31      0.0437041000
_diffrn_orient_matrix_UB_32      0.2128357000
_diffrn_orient_matrix_UB_33      -0.0123743000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0110
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4165
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.657
_diffrn_reflns_theta_min         4.570
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description
;
;
_exptl_crystal_F_000             264
_exptl_crystal_size_max          .18
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .08
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0555
_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/[σ²(Fo²)+(0.0803P)²+0.0855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1373
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1343
_reflns_number_total             1410
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b01704_si_002.cif
_cod_data_source_block           jcc13062r
_cod_depositor_comments
'Adding full bibliography for 1520575--1520576.cif.'
_cod_database_code               1520575
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2013-4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H14A(0.5) H14B(0.5) H14C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10)
3.b Idealised Me refined with riding coordinates:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'
3 '-x, -y, -z'
4 'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.72927(14) 0.2500 0.25128(13) 0.0435(4) Uani 1 2 d S T P . .
N2 N 0.97999(15) 0.2500 0.29934(15) 0.0492(4) Uani 1 2 d S T P . .
N3 N 0.5670(2) 0.2500 -0.22845(18) 0.0823(7) Uani 1 2 d S T P . .
C1 C 0.63418(16) 0.2500 0.13486(16) 0.0465(4) Uani 1 2 d S T P . .
H1 H 0.5388 0.2500 0.1332 0.056 Uiso 1 2 calc RS T P . .
C2 C 0.69800(16) 0.2500 0.01950(16) 0.0425(4) Uani 1 2 d S T P . .
C3 C 0.84303(15) 0.2500 0.06661(16) 0.0381(4) Uani 1 2 d S T P . .
C4 C 0.96347(16) 0.2500 0.00171(18) 0.0407(4) Uani 1 2 d S T P . .
C5 C 0.96373(19) 0.2500 -0.14173(19) 0.0495(4) Uani 1 2 d S T P . .
H5 H 0.8804 0.2500 -0.2024 0.059 Uiso 1 2 calc RS T P . .
C6 C 1.0872(2) 0.2500 -0.1923(2) 0.0618(5) Uani 1 2 d S T P . .
H6 H 1.0868 0.2500 -0.2873 0.074 Uiso 1 2 calc RS T P . .
C7 C 1.2128(2) 0.2500 -0.1032(3) 0.0701(6) Uani 1 2 d S T P . .
H7 H 1.2955 0.2500 -0.1389 0.084 Uiso 1 2 calc RS T P . .
C8 C 1.2151(2) 0.2500 0.0364(3) 0.0634(6) Uani 1 2 d S T P . .
H8 H 1.2997 0.2500 0.0950 0.076 Uiso 1 2 calc RS T P . .
C9 C 1.09058(17) 0.2500 0.0933(2) 0.0475(4) Uani 1 2 d S T P . .
C10 C 1.09046(17) 0.2500 0.2381(2) 0.0527(5) Uani 1 2 d S T P . .
H10 H 1.1762 0.2500 0.2948 0.063 Uiso 1 2 calc RS T P . .
C11 C 0.85937(16) 0.2500 0.21078(16) 0.0403(4) Uani 1 2 d S T P . .
C12 C 0.62607(17) 0.2500 -0.11808(17) 0.0532(5) Uani 1 2 d S T P . .
C13 C 0.69846(19) 0.2500 0.39653(16) 0.0480(4) Uani 1 2 d S T P . .
C14 C 0.5425(2) 0.2500 0.3939(2) 0.0623(5) Uani 1 2 d S T P . .
H14A H 0.5042 0.3692 0.3543 0.093 Uiso 0.5 1 calc R . . A -1
H14B H 0.5227 0.2377 0.4864 0.093 Uiso 0.5 1 calc R . . A -1
H14C H 0.5021 0.1431 0.3392 0.093 Uiso 0.5 1 calc R . . A -1
C15 C 0.75985(17) 0.0675(2) 0.46871(14) 0.0671(4) Uani 1 1 d . . . . .
H15A H 0.7206 -0.0443 0.4191 0.101 Uiso 1 1 calc R . . . .
H15B H 0.7393 0.0643 0.5614 0.101 Uiso 1 1 calc R . . . .
H15C H 0.8584 0.0675 0.4712 0.101 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C11 107.34(12) . .
C1 N1 C13 125.86(14) . .
C11 N1 C13 126.80(13) . .
C10 N2 C11 113.84(15) . .
N1 C1 H1 124.7 . .
N1 C1 C2 110.64(14) . .
C2 C1 H1 124.7 . .
C1 C2 C3 106.94(14) . .
C1 C2 C12 124.03(15) . .
C12 C2 C3 129.03(15) . .
C2 C3 C4 135.10(15) . .
C11 C3 C2 106.21(13) . .
C11 C3 C4 118.69(14) . .
C5 C4 C3 125.28(16) . .
C5 C4 C9 119.70(15) . .
C9 C4 C3 115.02(16) . .
C4 C5 H5 120.0 . .
C6 C5 C4 119.94(19) . .
C6 C5 H5 120.0 . .
C5 C6 H6 119.6 . .
C5 C6 C7 120.8(2) . .
C7 C6 H6 119.6 . .
C6 C7 H7 119.9 . .
C8 C7 C6 120.26(18) . .
C8 C7 H7 119.9 . .
C7 C8 H8 119.5 . .
C7 C8 C9 120.9(2) . .
C9 C8 H8 119.5 . .
C4 C9 C8 118.32(19) . .
C4 C9 C10 119.76(16) . .
C8 C9 C10 121.92(17) . .
N2 C10 C9 125.82(15) . .
N2 C10 H10 117.1 . .
C9 C10 H10 117.1 . .
N1 C11 C3 108.87(13) . .
N2 C11 N1 124.25(15) . .
N2 C11 C3 126.88(15) . .
N3 C12 C2 179.36(19) . .
N1 C13 C14 109.46(14) . .
N1 C13 C15 108.53(9) . 4_565
N1 C13 C15 108.53(9) . .
C14 C13 C15 109.25(10) . .
C14 C13 C15 109.25(10) . 4_565
C15 C13 C15 111.80(16) 4_565 .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.354(2) .
N1 C11 1.390(2) .
N1 C13 1.4996(19) .
N2 C10 1.315(2) .
N2 C11 1.350(2) .
N3 C12 1.144(2) .
C1 H1 0.9300 .
C1 C2 1.374(2) .
C2 C3 1.421(2) .
C2 C12 1.419(2) .
C3 C4 1.423(2) .
C3 C11 1.396(2) .
C4 C5 1.405(2) .
C4 C9 1.415(2) .
C5 H5 0.9300 .
C5 C6 1.375(3) .
C6 H6 0.9300 .
C6 C7 1.391(3) .
C7 H7 0.9300 .
C7 C8 1.364(4) .
C8 H8 0.9300 .
C8 C9 1.416(3) .
C9 C10 1.418(3) .
C10 H10 0.9300 .
C13 C14 1.521(3) .
C13 C15 1.5215(17) .
C13 C15 1.5215(17) 4_565
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
