#------------------------------------------------------------------------------
#$Date: 2023-05-05 03:44:28 +0300 (Fri, 05 May 2023) $
#$Revision: 283143 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/88/1568895.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_1568895
loop_
_publ_author_name
'Machida, Yutaro'
'Tanaka, Yudai'
'Masuda, Yuya'
'Kimura, Aya'
'Kawasaki, Tsuneomi'
_publ_section_title
;
 Chirally and chemically reversible Strecker reaction
;
_journal_issue                   17
_journal_name_full               'Chemical Science'
_journal_page_first              4480
_journal_page_last               4484
_journal_paper_doi               10.1039/D3SC00359K
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H20 N2'
_chemical_formula_sum            'C25 H20 N2'
_chemical_formula_weight         348.43
_chemical_name_common            1-Naph-aminonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-31
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-02 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.849(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.3374(3)
_cell_length_b                   6.0658(2)
_cell_length_c                   12.5814(4)
_cell_measurement_reflns_used    9460
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      136.44
_cell_measurement_theta_min      7.15
_cell_volume                     924.72(5)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10289
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.219
_diffrn_reflns_theta_min         3.577
_exptl_absorpt_coefficient_mu    0.564
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '[ABSCOR (Rigaku, 1995)]'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       needle
_exptl_crystal_F_000             368
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 905 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0364
_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)+(0.0429P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0786
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_full    0.805
_reflns_Friedel_fraction_max     0.799
_reflns_number_gt                2611
_reflns_number_total             3064
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc00359k2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
'Adding full bibliography for 1568893--1568896.cif.'
_cod_database_code               1568895
_shelx_shelxl_version_number     2018/3
_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   0.946
_shelx_estimated_absorpt_t_min   0.766
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C003(H003), C008(H008)
2.b Aromatic/amide H refined with riding coordinates:
 C005(H005), C009(H009), C00A(H00A), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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
N001 N 0.63917(16) 0.5237(4) 0.68418(16) 0.0205(5) Uani 1 1 d . . . . .
H001 H 0.5819(19) 0.601(5) 0.6570(19) 0.025 Uiso 1 1 d . U . . .
N002 N 0.54630(18) 0.3396(4) 0.42666(17) 0.0322(6) Uani 1 1 d . . . . .
C003 C 0.69491(19) 0.4643(4) 0.59518(18) 0.0199(6) Uani 1 1 d . . . . .
H003 H 0.745126 0.337257 0.619562 0.024 Uiso 1 1 calc R U . . .
C004 C 0.50944(18) 0.3816(5) 0.79621(18) 0.0205(6) Uani 1 1 d . . . . .
C005 C 0.75376(19) 0.3779(4) 0.90428(18) 0.0219(6) Uani 1 1 d . . . . .
H005 H 0.721995 0.517066 0.914733 0.026 Uiso 1 1 calc R U . . .
C006 C 0.8760(2) 0.6803(4) 0.62646(19) 0.0211(6) Uani 1 1 d . . . . .
C007 C 0.70493(18) 0.2442(4) 0.81825(18) 0.0187(5) Uani 1 1 d . . . . .
C008 C 0.60405(18) 0.3276(4) 0.73888(18) 0.0194(6) Uani 1 1 d . . . . .
H008 H 0.579422 0.210709 0.683548 0.023 Uiso 1 1 calc R U . . .
C009 C 0.7224(2) 0.8027(5) 0.48855(19) 0.0242(6) Uani 1 1 d . . . . .
H009 H 0.649774 0.781268 0.448559 0.029 Uiso 1 1 calc R U . . .
C00A C 0.9301(2) 0.5268(5) 0.70307(19) 0.0251(6) Uani 1 1 d . . . . .
H00A H 0.891762 0.398834 0.719054 0.030 Uiso 1 1 calc R U . . .
C00B C 0.76497(19) 0.6539(4) 0.56698(18) 0.0203(6) Uani 1 1 d . . . . .
C00C C 0.6133(2) 0.3921(4) 0.4983(2) 0.0238(6) Uani 1 1 d . . . . .
C00D C 0.43180(19) 0.2185(5) 0.8043(2) 0.0241(6) Uani 1 1 d . . . . .
H00D H 0.435791 0.080500 0.769517 0.029 Uiso 1 1 calc R U . . .
C00E C 0.50079(19) 0.5840(5) 0.84635(18) 0.0242(6) Uani 1 1 d . . . . .
H00E H 0.551951 0.698181 0.840177 0.029 Uiso 1 1 calc R U . . .
C00F C 0.75271(19) 0.0420(5) 0.80381(19) 0.0247(6) Uani 1 1 d . . . . .
H00F H 0.719688 -0.051864 0.746324 0.030 Uiso 1 1 calc R U . . .
C00G C 0.84764(19) 0.3103(5) 0.97430(19) 0.0252(6) Uani 1 1 d . . . . .
H00G H 0.879498 0.401377 1.033380 0.030 Uiso 1 1 calc R U . . .
C00H C 0.8868(2) 1.0229(5) 0.5243(2) 0.0293(6) Uani 1 1 d . . . . .
H00H H 0.926751 1.150146 0.510344 0.035 Uiso 1 1 calc R U . . .
C00I C 0.8955(2) 0.1090(5) 0.9583(2) 0.0296(7) Uani 1 1 d . . . . .
H00I H 0.960470 0.062942 1.006271 0.036 Uiso 1 1 calc R U . . .
C00J C 0.9351(2) 0.8730(5) 0.6056(2) 0.0254(6) Uani 1 1 d . . . . .
C00K C 1.0445(2) 0.9049(5) 0.6636(2) 0.0307(7) Uani 1 1 d . . . . .
H00K H 1.083630 1.034733 0.651787 0.037 Uiso 1 1 calc R U . . .
C00L C 0.8492(2) -0.0241(5) 0.8734(2) 0.0295(6) Uani 1 1 d . . . . .
H00L H 0.882702 -0.160901 0.862057 0.035 Uiso 1 1 calc R U . . .
C00M C 0.7835(2) 0.9872(5) 0.4656(2) 0.0300(7) Uani 1 1 d . . . . .
H00M H 0.752964 1.086305 0.409450 0.036 Uiso 1 1 calc R U . . .
C00N C 0.4181(2) 0.6198(5) 0.9052(2) 0.0292(7) Uani 1 1 d . . . . .
H00N H 0.413232 0.758015 0.939510 0.035 Uiso 1 1 calc R U . . .
C00O C 0.3488(2) 0.2563(5) 0.8626(2) 0.0300(7) Uani 1 1 d . . . . .
H00O H 0.295900 0.144475 0.867104 0.036 Uiso 1 1 calc R U . . .
C00P C 0.3426(2) 0.4559(5) 0.9142(2) 0.0313(7) Uani 1 1 d . . . . .
H00P H 0.286764 0.480247 0.955547 0.038 Uiso 1 1 calc R U . . .
C00Q C 1.0369(2) 0.5597(5) 0.75456(19) 0.0306(7) Uani 1 1 d . . . . .
H00Q H 1.072789 0.451431 0.803426 0.037 Uiso 1 1 calc R U . . .
C00R C 1.0940(2) 0.7518(5) 0.7359(2) 0.0349(8) Uani 1 1 d . . . . .
H00R H 1.167313 0.774942 0.773712 0.042 Uiso 1 1 calc R U . . .
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
C003 N001 H001 107.3(16) . . ?
C003 N001 C008 112.2(2) . . ?
C008 N001 H001 109.4(18) . . ?
N001 C003 H003 107.9 . . ?
N001 C003 C00B 111.2(2) . . ?
N001 C003 C00C 110.80(19) . . ?
C00B C003 H003 107.9 . . ?
C00C C003 H003 107.9 . . ?
C00C C003 C00B 110.89(19) . . ?
C00D C004 C008 118.8(2) . . ?
C00E C004 C008 122.4(2) . . ?
C00E C004 C00D 118.7(2) . . ?
C007 C005 H005 119.7 . . ?
C00G C005 H005 119.7 . . ?
C00G C005 C007 120.7(2) . . ?
C00A C006 C00B 124.2(2) . . ?
C00A C006 C00J 118.2(2) . . ?
C00J C006 C00B 117.6(2) . . ?
C005 C007 C008 119.6(2) . . ?
C00F C007 C005 118.9(2) . . ?
C00F C007 C008 121.4(2) . . ?
N001 C008 C004 111.5(2) . . ?
N001 C008 C007 107.24(19) . . ?
N001 C008 H008 108.9 . . ?
C004 C008 C007 111.42(18) . . ?
C004 C008 H008 108.9 . . ?
C007 C008 H008 108.9 . . ?
C00B C009 H009 119.2 . . ?
C00B C009 C00M 121.6(2) . . ?
C00M C009 H009 119.2 . . ?
C006 C00A H00A 119.5 . . ?
C00Q C00A C006 121.0(3) . . ?
C00Q C00A H00A 119.5 . . ?
C006 C00B C003 119.3(2) . . ?
C009 C00B C003 120.6(2) . . ?
C009 C00B C006 120.0(2) . . ?
N002 C00C C003 176.4(3) . . ?
C004 C00D H00D 119.8 . . ?
C00O C00D C004 120.5(3) . . ?
C00O C00D H00D 119.8 . . ?
C004 C00E H00E 119.8 . . ?
C00N C00E C004 120.4(2) . . ?
C00N C00E H00E 119.8 . . ?
C007 C00F H00F 119.8 . . ?
C007 C00F C00L 120.3(2) . . ?
C00L C00F H00F 119.8 . . ?
C005 C00G H00G 120.0 . . ?
C005 C00G C00I 119.9(2) . . ?
C00I C00G H00G 120.0 . . ?
C00J C00H H00H 119.6 . . ?
C00M C00H H00H 119.6 . . ?
C00M C00H C00J 120.9(3) . . ?
C00G C00I H00I 119.9 . . ?
C00L C00I C00G 120.2(2) . . ?
C00L C00I H00I 119.9 . . ?
C00H C00J C006 120.0(2) . . ?
C00H C00J C00K 121.0(3) . . ?
C00K C00J C006 119.0(2) . . ?
C00J C00K H00K 119.6 . . ?
C00R C00K C00J 120.9(3) . . ?
C00R C00K H00K 119.6 . . ?
C00F C00L H00L 120.0 . . ?
C00I C00L C00F 119.9(3) . . ?
C00I C00L H00L 120.0 . . ?
C009 C00M H00M 120.1 . . ?
C00H C00M C009 119.8(3) . . ?
C00H C00M H00M 120.1 . . ?
C00E C00N H00N 119.8 . . ?
C00P C00N C00E 120.4(3) . . ?
C00P C00N H00N 119.8 . . ?
C00D C00O H00O 119.9 . . ?
C00P C00O C00D 120.3(3) . . ?
C00P C00O H00O 119.9 . . ?
C00N C00P C00O 119.6(2) . . ?
C00N C00P H00P 120.2 . . ?
C00O C00P H00P 120.2 . . ?
C00A C00Q H00Q 119.7 . . ?
C00A C00Q C00R 120.7(3) . . ?
C00R C00Q H00Q 119.7 . . ?
C00K C00R C00Q 120.1(2) . . ?
C00K C00R H00R 119.9 . . ?
C00Q C00R H00R 119.9 . . ?
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
N001 H001 0.86(3) . ?
N001 C003 1.465(3) . ?
N001 C008 1.479(3) . ?
N002 C00C 1.148(3) . ?
C003 H003 1.0000 . ?
C003 C00B 1.520(3) . ?
C003 C00C 1.493(3) . ?
C004 C008 1.519(3) . ?
C004 C00D 1.394(3) . ?
C004 C00E 1.394(4) . ?
C005 H005 0.9500 . ?
C005 C007 1.395(3) . ?
C005 C00G 1.379(3) . ?
C006 C00A 1.414(3) . ?
C006 C00B 1.441(3) . ?
C006 C00J 1.428(3) . ?
C007 C008 1.528(3) . ?
C007 C00F 1.387(3) . ?
C008 H008 1.0000 . ?
C009 H009 0.9500 . ?
C009 C00B 1.367(3) . ?
C009 C00M 1.410(4) . ?
C00A H00A 0.9500 . ?
C00A C00Q 1.369(3) . ?
C00D H00D 0.9500 . ?
C00D C00O 1.387(3) . ?
C00E H00E 0.9500 . ?
C00E C00N 1.386(3) . ?
C00F H00F 0.9500 . ?
C00F C00L 1.397(3) . ?
C00G H00G 0.9500 . ?
C00G C00I 1.387(4) . ?
C00H H00H 0.9500 . ?
C00H C00J 1.413(4) . ?
C00H C00M 1.364(4) . ?
C00I H00I 0.9500 . ?
C00I C00L 1.375(4) . ?
C00J C00K 1.422(3) . ?
C00K H00K 0.9500 . ?
C00K C00R 1.361(4) . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00N H00N 0.9500 . ?
C00N C00P 1.381(4) . ?
C00O H00O 0.9500 . ?
C00O C00P 1.383(4) . ?
C00P H00P 0.9500 . ?
C00Q H00Q 0.9500 . ?
C00Q C00R 1.404(4) . ?
C00R H00R 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N001 C003 C00B C006 85.5(3) . . . . ?
N001 C003 C00B C009 -92.4(3) . . . . ?
C003 N001 C008 C004 -156.63(18) . . . . ?
C003 N001 C008 C007 81.2(2) . . . . ?
C004 C00D C00O C00P -0.5(4) . . . . ?
C004 C00E C00N C00P -0.5(4) . . . . ?
C005 C007 C008 N001 63.2(2) . . . . ?
C005 C007 C008 C004 -59.1(3) . . . . ?
C005 C007 C00F C00L -1.1(3) . . . . ?
C005 C00G C00I C00L -0.5(4) . . . . ?
C006 C00A C00Q C00R 2.7(4) . . . . ?
C006 C00J C00K C00R 1.9(4) . . . . ?
C007 C005 C00G C00I 1.1(4) . . . . ?
C007 C00F C00L C00I 1.7(4) . . . . ?
C008 N001 C003 C00B -159.67(19) . . . . ?
C008 N001 C003 C00C 76.5(3) . . . . ?
C008 C004 C00D C00O 175.4(2) . . . . ?
C008 C004 C00E C00N -174.8(2) . . . . ?
C008 C007 C00F C00L 175.8(2) . . . . ?
C00A C006 C00B C003 7.1(3) . . . . ?
C00A C006 C00B C009 -175.0(2) . . . . ?
C00A C006 C00J C00H 175.6(2) . . . . ?
C00A C006 C00J C00K -1.1(3) . . . . ?
C00A C00Q C00R C00K -1.9(4) . . . . ?
C00B C006 C00A C00Q 178.2(2) . . . . ?
C00B C006 C00J C00H -3.7(3) . . . . ?
C00B C006 C00J C00K 179.5(2) . . . . ?
C00B C009 C00M C00H -1.7(4) . . . . ?
C00C C003 C00B C006 -150.8(2) . . . . ?
C00C C003 C00B C009 31.4(3) . . . . ?
C00D C004 C008 N001 148.3(2) . . . . ?
C00D C004 C008 C007 -92.0(3) . . . . ?
C00D C004 C00E C00N 1.5(3) . . . . ?
C00D C00O C00P C00N 1.5(4) . . . . ?
C00E C004 C008 N001 -35.4(3) . . . . ?
C00E C004 C008 C007 84.3(3) . . . . ?
C00E C004 C00D C00O -1.1(3) . . . . ?
C00E C00N C00P C00O -1.1(4) . . . . ?
C00F C007 C008 N001 -113.6(2) . . . . ?
C00F C007 C008 C004 124.1(2) . . . . ?
C00G C005 C007 C008 -177.2(2) . . . . ?
C00G C005 C007 C00F -0.3(3) . . . . ?
C00G C00I C00L C00F -0.9(4) . . . . ?
C00H C00J C00K C00R -174.9(2) . . . . ?
C00J C006 C00A C00Q -1.1(3) . . . . ?
C00J C006 C00B C003 -173.5(2) . . . . ?
C00J C006 C00B C009 4.3(3) . . . . ?
C00J C00H C00M C009 2.2(4) . . . . ?
C00J C00K C00R C00Q -0.4(4) . . . . ?
C00M C009 C00B C003 176.1(2) . . . . ?
C00M C009 C00B C006 -1.7(3) . . . . ?
C00M C00H C00J C006 0.5(4) . . . . ?
C00M C00H C00J C00K 177.2(2) . . . . ?
