#------------------------------------------------------------------------------
#$Date: 2022-05-05 03:36:13 +0300 (Thu, 05 May 2022) $
#$Revision: 274903 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158664.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_7158664
loop_
_publ_author_name
'Mikshiev, Vladimir Y.'
'Tolstoy, Peter'
'Puzyk, Aleksandra M.'
'Kirichenko, Sergey O.'
'Antonov, Alexander S.'
_publ_section_title
;
 peri-Interactions in 1,8-bis(dimethylamino)naphthalene ortho-ketimine
 cations facilitate [1,5]-hydride shift: selective synthesis of
 1,2,3,4-tetrahydrobenzo[h]quinazolines
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00674J
_journal_year                    2022
_chemical_formula_moiety         'C19 H27 N3'
_chemical_formula_sum            'C19 H27 N3'
_chemical_formula_weight         297.43
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc29hxc3
_audit_creation_date             2021-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-22 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6026(2)
_cell_length_b                   12.0411(3)
_cell_length_c                   14.2206(4)
_cell_measurement_reflns_used    6112
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      77.1700
_cell_measurement_theta_min      5.8860
_cell_volume                     1644.27(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00  22.00   0.50    0.30    --  -47.10  93.00  93.00  186
  2  ω   -176.00 -92.00   0.50    1.50    -- -106.00 -44.00  91.00  168
  3  ω   -139.00 -84.00   0.50    1.50    -- -106.00 -93.00 -18.00  110
  4  ω     45.00 101.00   0.50    1.50    --  113.25 -92.00-119.00  112
  5  ω    -24.00  22.00   0.50    0.30    --   47.10 -19.00-150.00   92
  6  ω    -25.00  22.00   0.50    0.30    --   47.10 -19.00 -30.00   94
  7  ω    -64.00 -35.00   0.50    1.50    -- -106.00  61.00  90.00   58
  8  ω     42.00  68.00   0.50    1.50    --  113.25 -61.00 -90.00   52
  9  ω     42.00  68.00   0.50    1.50    --  113.25 -61.00-180.00   52
 10  ω     62.00 101.00   0.50    1.50    --  113.25 -94.00 150.00   78
 11  ω     45.00  70.00   0.50    1.50    --  113.25 -61.00  60.00   50
 12  ω     43.00 111.00   0.50    1.50    --  113.25-125.00  30.00  136
 13  ω     43.00  71.00   0.50    1.50    --  113.25 -94.00 -90.00   56
 14  ω     84.00 137.00   0.50    1.50    --  113.25  92.00  -6.00  106
 15  ω    -13.00  16.00   0.50    0.30    --  -47.10  19.00-180.00   58
 16  ω   -104.00 -74.00   0.50    0.30    --  -47.10-125.00-150.00   60
 17  ω   -149.00 -99.00   0.50    1.50    -- -106.00 -77.00 -30.00  100
 18  ω   -176.00-151.00   0.50    1.50    -- -106.00 -45.00 -90.00   50
 19  ω   -172.00-120.00   0.50    1.50    -- -106.00 -45.00-180.00  104
 20  ω    -95.00 -49.00   0.50    1.50    -- -106.00  77.00  60.00   92
 21  ω   -121.00 -93.00   0.50    1.50    -- -106.00 -45.00 -90.00   56
 22  ω    -71.00 -39.00   0.50    1.50    -- -106.00  77.00  90.00   64
 23  ω   -100.00 -74.00   0.50    1.50    -- -106.00  77.00  90.00   52
 24  ω     73.00 104.00   0.50    1.50    --  113.25 -94.00-180.00   62
 25  ω     43.00  69.00   0.50    1.50    --  113.25 -61.00-150.00   52
 26  ω    149.00 176.00   0.50    1.50    --  113.25  45.00  60.00   54
 27  ω    107.00 133.00   0.50    1.50    --  113.25  45.00  60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0852714000
_diffrn_orient_matrix_UB_12      -0.0533579000
_diffrn_orient_matrix_UB_13      0.0798354000
_diffrn_orient_matrix_UB_21      0.0205700000
_diffrn_orient_matrix_UB_22      0.1050526000
_diffrn_orient_matrix_UB_23      0.0603019000
_diffrn_orient_matrix_UB_31      -0.1342996000
_diffrn_orient_matrix_UB_32      0.0498258000
_diffrn_orient_matrix_UB_33      -0.0416151000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10544
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.960
_diffrn_reflns_theta_min         5.559
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1159 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0335
_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)+(0.0612P)²+0.0672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                2876
_reflns_number_total             3091
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00674j2.cif
_cod_data_source_block           20015_lja-6_auto
_cod_database_code               7158664
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C19 H27 N3'
_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.
;
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.899
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C8(H8), C11(H11), C7(H7)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C19(H19A,H19B,
 H19C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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 1.581
_oxdiff_exptl_absorpt_empirical_full_min 0.608
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
N2 N 0.65103(14) 0.36767(12) 0.40469(11) 0.0206(3) Uani 1 1 d . . . . .
N3 N 0.59035(14) 0.13644(13) 0.40411(11) 0.0212(3) Uani 1 1 d . . . . .
N1 N 0.50384(16) 0.53295(13) 0.39786(11) 0.0260(3) Uani 1 1 d . . . . .
C6 C 0.61978(16) 0.14430(15) 0.50008(12) 0.0190(4) Uani 1 1 d . . . . .
C4 C 0.61511(17) 0.35734(15) 0.49861(12) 0.0189(4) Uani 1 1 d . . . . .
C5 C 0.61792(15) 0.25149(14) 0.54629(13) 0.0187(4) Uani 1 1 d . . . . .
C9 C 0.64242(18) 0.15294(16) 0.69759(13) 0.0229(4) Uani 1 1 d . . . . .
H9 H 0.6465 0.1545 0.7643 0.027 Uiso 1 1 calc R . . . .
C10 C 0.61528(16) 0.25243(15) 0.64711(13) 0.0210(4) Uani 1 1 d . . . . .
C12 C 0.55432(19) 0.44664(16) 0.64587(13) 0.0238(4) Uani 1 1 d . . . . .
H12 H 0.5212 0.5103 0.6784 0.029 Uiso 1 1 calc R . . . .
C8 C 0.66266(17) 0.05507(16) 0.65091(13) 0.0237(4) Uani 1 1 d . . . . .
H8 H 0.6864 -0.0100 0.6851 0.028 Uiso 1 1 calc R . . . .
C11 C 0.58118(18) 0.35140(16) 0.69518(12) 0.0237(4) Uani 1 1 d . . . . .
H11 H 0.5769 0.3519 0.7619 0.028 Uiso 1 1 calc R . . . .
C7 C 0.64857(18) 0.05006(15) 0.55262(13) 0.0226(4) Uani 1 1 d . . . . .
H7 H 0.6590 -0.0193 0.5216 0.027 Uiso 1 1 calc R . . . .
C3 C 0.57458(17) 0.45239(15) 0.54829(12) 0.0218(4) Uani 1 1 d . . . . .
C15 C 0.6313(2) 0.03675(16) 0.35428(13) 0.0256(4) Uani 1 1 d . . . . .
H15A H 0.7276 0.0179 0.3705 0.038 Uiso 1 1 calc GR . . . .
H15B H 0.6242 0.0495 0.2864 0.038 Uiso 1 1 calc GR . . . .
H15C H 0.5697 -0.0246 0.3723 0.038 Uiso 1 1 calc GR . . . .
C13 C 0.77164(18) 0.31330(16) 0.36431(13) 0.0239(4) Uani 1 1 d . . . . .
H13A H 0.8419 0.3691 0.3481 0.036 Uiso 1 1 calc GR . . . .
H13B H 0.7439 0.2729 0.3075 0.036 Uiso 1 1 calc GR . . . .
H13C H 0.8108 0.2610 0.4101 0.036 Uiso 1 1 calc GR . . . .
C2 C 0.55420(18) 0.55894(16) 0.49374(12) 0.0239(4) Uani 1 1 d . . . . .
H2 H 0.4762 0.5990 0.5256 0.029 Uiso 1 1 calc R . . . .
C16 C 0.6810(2) 0.64107(15) 0.49443(13) 0.0255(4) Uani 1 1 d . . . . .
C14 C 0.45985(18) 0.18290(16) 0.36899(12) 0.0241(4) Uani 1 1 d . . . . .
H14A H 0.3880 0.1251 0.3688 0.036 Uiso 1 1 calc GR . . . .
H14B H 0.4736 0.2106 0.3049 0.036 Uiso 1 1 calc GR . . . .
H14C H 0.4304 0.2442 0.4098 0.036 Uiso 1 1 calc GR . . . .
C1 C 0.59461(18) 0.45833(16) 0.34790(13) 0.0245(4) Uani 1 1 d . . . . .
H1A H 0.6732 0.5016 0.3217 0.029 Uiso 1 1 calc R . . . .
H1B H 0.5426 0.4261 0.2944 0.029 Uiso 1 1 calc R . . . .
C19 C 0.6601(2) 0.72969(16) 0.41890(14) 0.0302(4) Uani 1 1 d . . . . .
H19A H 0.6677 0.6955 0.3566 0.045 Uiso 1 1 calc GR . . . .
H19B H 0.7316 0.7872 0.4256 0.045 Uiso 1 1 calc GR . . . .
H19C H 0.5677 0.7632 0.4260 0.045 Uiso 1 1 calc GR . . . .
C17 C 0.8213(2) 0.58292(16) 0.47840(15) 0.0296(4) Uani 1 1 d . . . . .
H17A H 0.8312 0.5214 0.5230 0.044 Uiso 1 1 calc GR . . . .
H17B H 0.8972 0.6362 0.4879 0.044 Uiso 1 1 calc GR . . . .
H17C H 0.8252 0.5541 0.4140 0.044 Uiso 1 1 calc GR . . . .
C18 C 0.6868(3) 0.69738(18) 0.59059(15) 0.0385(5) Uani 1 1 d . . . . .
H18A H 0.5981 0.7350 0.6029 0.058 Uiso 1 1 calc GR . . . .
H18B H 0.7625 0.7519 0.5913 0.058 Uiso 1 1 calc GR . . . .
H18C H 0.7034 0.6414 0.6393 0.058 Uiso 1 1 calc GR . . . .
H1 H 0.415(3) 0.5021(19) 0.4055(16) 0.027(6) Uiso 1 1 d . . . . .
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
_geom_angle_publ_flag
C4 N2 C13 122.73(15) . . ?
C4 N2 C1 120.50(15) . . ?
C13 N2 C1 114.50(14) . . ?
C6 N3 C15 118.64(15) . . ?
C6 N3 C14 118.80(15) . . ?
C15 N3 C14 112.53(14) . . ?
C1 N1 C2 112.87(14) . . ?
N3 C6 C5 120.08(16) . . ?
C7 C6 N3 120.75(16) . . ?
C7 C6 C5 119.16(16) . . ?
N2 C4 C5 121.83(16) . . ?
N2 C4 C3 118.84(16) . . ?
C3 C4 C5 119.33(16) . . ?
C4 C5 C6 125.01(16) . . ?
C10 C5 C6 117.45(16) . . ?
C10 C5 C4 117.53(16) . . ?
C8 C9 C10 120.52(17) . . ?
C9 C10 C5 119.69(17) . . ?
C11 C10 C5 119.65(17) . . ?
C11 C10 C9 120.63(17) . . ?
C11 C12 C3 121.47(18) . . ?
C9 C8 C7 120.42(17) . . ?
C12 C11 C10 120.18(16) . . ?
C6 C7 C8 121.33(17) . . ?
C4 C3 C12 119.82(17) . . ?
C4 C3 C2 118.08(15) . . ?
C12 C3 C2 122.11(17) . . ?
N1 C2 C3 109.61(15) . . ?
N1 C2 C16 113.12(14) . . ?
C3 C2 C16 115.55(14) . . ?
C19 C16 C2 109.52(16) . . ?
C19 C16 C17 109.22(16) . . ?
C19 C16 C18 108.92(16) . . ?
C17 C16 C2 113.13(15) . . ?
C18 C16 C2 108.28(15) . . ?
C18 C16 C17 107.67(17) . . ?
N1 C1 N2 114.70(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C4 1.385(2) . ?
N2 C13 1.449(2) . ?
N2 C1 1.462(2) . ?
N3 C6 1.397(2) . ?
N3 C15 1.448(2) . ?
N3 C14 1.460(2) . ?
N1 C2 1.480(2) . ?
N1 C1 1.439(2) . ?
C6 C5 1.448(3) . ?
C6 C7 1.386(3) . ?
C4 C5 1.444(3) . ?
C4 C3 1.400(3) . ?
C5 C10 1.434(2) . ?
C9 C10 1.421(3) . ?
C9 C8 1.366(3) . ?
C10 C11 1.412(3) . ?
C12 C11 1.369(3) . ?
C12 C3 1.403(3) . ?
C8 C7 1.406(3) . ?
C3 C2 1.512(3) . ?
C2 C16 1.569(3) . ?
C16 C19 1.527(3) . ?
C16 C17 1.536(3) . ?
C16 C18 1.527(3) . ?
