#------------------------------------------------------------------------------
#$Date: 2022-08-24 12:08:28 +0300 (Wed, 24 Aug 2022) $
#$Revision: 277381 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/56/8105697.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_8105697
loop_
_publ_author_name
'Zhang, Qiu Yu'
'Yu, Yu'
_publ_section_title
;
 Crystal structure of 9-methoxy-2,3,4,4a,5,6-hexahydro-1H-pyrido
 [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C15H18N4O
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              361
_journal_page_last               363
_journal_paper_doi               10.1515/ncrs-2022-0012
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C15 H18 N4 O'
_chemical_formula_sum            'C15 H18 N4 O'
_chemical_formula_weight         270.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                97.206(5)
_cell_angle_beta                 102.335(6)
_cell_angle_gamma                108.614(7)
_cell_formula_units_Z            2
_cell_length_a                   6.7562(5)
_cell_length_b                   9.5520(6)
_cell_length_c                   11.4227(8)
_cell_measurement_reflns_used    2109
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      29.2640
_cell_measurement_theta_min      2.6240
_cell_volume                     667.39(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -79.00  10.00   1.00    1.60    --  -11.51 -57.00-150.00   89
  2  ω    -40.00  59.00   1.00    1.60    --  -11.51  57.00   0.00   99
  3  ω    -13.00  76.00   1.00    1.60    --   12.05  77.00 120.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0904011000
_diffrn_orient_matrix_UB_12      -0.0174543000
_diffrn_orient_matrix_UB_13      -0.0514325000
_diffrn_orient_matrix_UB_21      0.0686814000
_diffrn_orient_matrix_UB_22      0.0037840000
_diffrn_orient_matrix_UB_23      -0.0395052000
_diffrn_orient_matrix_UB_31      -0.0186011000
_diffrn_orient_matrix_UB_32      -0.0781116000
_diffrn_orient_matrix_UB_33      -0.0043662000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4208
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.301
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.345
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0480
_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)+(0.0720P)²+0.1369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1388
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1896
_reflns_number_total             2346
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0012_suppl.cif
_cod_data_source_block           stna-3
_cod_database_code               8105697
_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 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C10(H10), C11(H11), C13(H13)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_olex2_date_sample_data_collection 2021-11-24
_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 1.364
_oxdiff_exptl_absorpt_empirical_full_min 0.795
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.13061(17) 0.42481(12) 0.13536(10) 0.0290(3) Uani 1 1 d . . . . .
N1 N 0.6458(2) 0.17601(14) 0.69722(11) 0.0211(3) Uani 1 1 d . . . . .
N2 N 0.95986(19) 0.36062(14) 0.60444(11) 0.0225(3) Uani 1 1 d . . . . .
H2 H 1.057240 0.413802 0.574076 0.027 Uiso 1 1 calc R U . . .
N3 N 0.3767(2) 0.19211(14) 0.53973(11) 0.0211(3) Uani 1 1 d . . . . .
N4 N 0.69975(19) 0.38572(13) 0.45230(11) 0.0195(3) Uani 1 1 d . . . . .
C1 C 0.4747(3) 0.05508(18) 0.72461(14) 0.0280(4) Uani 1 1 d . . . . .
H1A H 0.439908 -0.038301 0.666618 0.034 Uiso 1 1 calc R U . . .
H1B H 0.344944 0.080452 0.714896 0.034 Uiso 1 1 calc R U . . .
C2 C 0.5431(3) 0.0319(2) 0.85271(15) 0.0335(4) Uani 1 1 d . . . . .
H2A H 0.558185 0.120326 0.910888 0.040 Uiso 1 1 calc R U . . .
H2B H 0.431362 -0.054031 0.864890 0.040 Uiso 1 1 calc R U . . .
C3 C 0.7540(3) 0.0050(2) 0.87684(16) 0.0350(4) Uani 1 1 d . . . . .
H3A H 0.735549 -0.089384 0.825127 0.042 Uiso 1 1 calc R U . . .
H3B H 0.798266 -0.002535 0.961657 0.042 Uiso 1 1 calc R U . . .
C4 C 0.9272(3) 0.13371(19) 0.85060(14) 0.0290(4) Uani 1 1 d . . . . .
H4A H 1.058172 0.109911 0.858984 0.035 Uiso 1 1 calc R U . . .
H4B H 0.960553 0.224401 0.911371 0.035 Uiso 1 1 calc R U . . .
C5 C 0.8621(2) 0.16554(17) 0.72356(14) 0.0259(4) Uani 1 1 d . . . . .
H5 H 0.859812 0.082446 0.662865 0.031 Uiso 1 1 calc R U . . .
C6 C 1.0276(2) 0.30955(18) 0.71385(14) 0.0248(4) Uani 1 1 d . . . . .
H6A H 1.054731 0.387593 0.784598 0.030 Uiso 1 1 calc R U . . .
H6B H 1.162729 0.293532 0.715075 0.030 Uiso 1 1 calc R U . . .
C7 C 0.7503(2) 0.32845(16) 0.54783(13) 0.0179(3) Uani 1 1 d . . . . .
C8 C 0.5820(2) 0.22788(16) 0.59313(13) 0.0189(3) Uani 1 1 d . . . . .
C9 C 0.3223(2) 0.25400(16) 0.44026(13) 0.0204(4) Uani 1 1 d . . . . .
C10 C 0.1034(2) 0.22143(17) 0.38113(14) 0.0241(4) Uani 1 1 d . . . . .
H10 H -0.003985 0.158675 0.409732 0.029 Uiso 1 1 calc R U . . .
C11 C 0.0459(3) 0.28071(18) 0.28207(14) 0.0263(4) Uani 1 1 d . . . . .
H11 H -0.099847 0.259365 0.244387 0.032 Uiso 1 1 calc R U . . .
C12 C 0.2066(2) 0.37386(17) 0.23708(13) 0.0233(4) Uani 1 1 d . . . . .
C13 C 0.4227(2) 0.40793(17) 0.29314(13) 0.0221(4) Uani 1 1 d . . . . .
H13 H 0.528474 0.469533 0.262840 0.027 Uiso 1 1 calc R U . . .
C14 C 0.4832(2) 0.34936(16) 0.39633(13) 0.0188(4) Uani 1 1 d . . . . .
C15 C 0.2883(3) 0.5066(2) 0.08046(15) 0.0333(4) Uani 1 1 d . . . . .
H15A H 0.217304 0.532332 0.008607 0.050 Uiso 1 1 calc R U . . .
H15B H 0.368249 0.445502 0.057984 0.050 Uiso 1 1 calc R U . . .
H15C H 0.385878 0.597305 0.137671 0.050 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C12 O1 C15 116.49(12) . .
C5 N1 C1 116.25(12) . .
C8 N1 C1 115.63(12) . .
C8 N1 C5 116.91(11) . .
C6 N2 H2 118.8 . .
C7 N2 H2 118.8 . .
C7 N2 C6 122.43(12) . .
C8 N3 C9 117.65(12) . .
C7 N4 C14 117.57(12) . .
N1 C1 H1A 109.3 . .
N1 C1 H1B 109.3 . .
N1 C1 C2 111.76(13) . .
H1A C1 H1B 107.9 . .
C2 C1 H1A 109.3 . .
C2 C1 H1B 109.3 . .
C1 C2 H2A 109.3 . .
C1 C2 H2B 109.3 . .
H2A C2 H2B 107.9 . .
C3 C2 C1 111.81(13) . .
C3 C2 H2A 109.3 . .
C3 C2 H2B 109.3 . .
C2 C3 H3A 109.7 . .
C2 C3 H3B 109.7 . .
C2 C3 C4 109.97(13) . .
H3A C3 H3B 108.2 . .
C4 C3 H3A 109.7 . .
C4 C3 H3B 109.7 . .
C3 C4 H4A 108.8 . .
C3 C4 H4B 108.8 . .
C3 C4 C5 113.59(13) . .
H4A C4 H4B 107.7 . .
C5 C4 H4A 108.8 . .
C5 C4 H4B 108.8 . .
N1 C5 C4 111.41(12) . .
N1 C5 H5 108.5 . .
N1 C5 C6 110.34(12) . .
C4 C5 H5 108.5 . .
C6 C5 C4 109.46(13) . .
C6 C5 H5 108.5 . .
N2 C6 C5 112.73(12) . .
N2 C6 H6A 109.0 . .
N2 C6 H6B 109.0 . .
C5 C6 H6A 109.0 . .
C5 C6 H6B 109.0 . .
H6A C6 H6B 107.8 . .
N2 C7 C8 119.34(13) . .
N4 C7 N2 119.30(13) . .
N4 C7 C8 121.35(13) . .
N1 C8 C7 118.51(13) . .
N3 C8 N1 120.17(13) . .
N3 C8 C7 121.28(13) . .
N3 C9 C10 119.84(13) . .
N3 C9 C14 121.08(14) . .
C10 C9 C14 119.08(14) . .
C9 C10 H10 119.6 . .
C11 C10 C9 120.83(14) . .
C11 C10 H10 119.6 . .
C10 C11 H11 120.0 . .
C10 C11 C12 120.05(14) . .
C12 C11 H11 120.0 . .
O1 C12 C11 115.21(13) . .
C13 C12 O1 124.31(14) . .
C13 C12 C11 120.48(14) . .
C12 C13 H13 120.1 . .
C12 C13 C14 119.81(14) . .
C14 C13 H13 120.1 . .
N4 C14 C9 121.05(13) . .
N4 C14 C13 119.20(13) . .
C13 C14 C9 119.74(14) . .
O1 C15 H15A 109.5 . .
O1 C15 H15B 109.5 . .
O1 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
O1 C12 1.3774(18) .
O1 C15 1.420(2) .
N1 C1 1.4699(19) .
N1 C5 1.4662(19) .
N1 C8 1.3820(18) .
N2 H2 0.8600 .
N2 C6 1.4354(18) .
N2 C7 1.3411(19) .
N3 C8 1.303(2) .
N3 C9 1.3800(19) .
N4 C7 1.3100(18) .
N4 C14 1.3746(19) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C1 C2 1.504(2) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C2 C3 1.502(2) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C3 C4 1.515(2) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C4 C5 1.522(2) .
C5 H5 0.9800 .
C5 C6 1.505(2) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.470(2) .
C9 C10 1.403(2) .
C9 C14 1.407(2) .
C10 H10 0.9300 .
C10 C11 1.366(2) .
C11 H11 0.9300 .
C11 C12 1.404(2) .
C12 C13 1.376(2) .
C13 H13 0.9300 .
C13 C14 1.405(2) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
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
O1 C12 C13 C14 -179.66(12) . . . .
N1 C1 C2 C3 -54.16(19) . . . .
N1 C5 C6 N2 -47.34(17) . . . .
N2 C7 C8 N1 3.4(2) . . . .
N2 C7 C8 N3 -179.03(13) . . . .
N3 C9 C10 C11 -179.60(12) . . . .
N3 C9 C14 N4 -1.0(2) . . . .
N3 C9 C14 C13 178.57(11) . . . .
N4 C7 C8 N1 -177.47(11) . . . .
N4 C7 C8 N3 0.1(2) . . . .
C1 N1 C5 C4 -47.61(18) . . . .
C1 N1 C5 C6 -169.41(12) . . . .
C1 N1 C8 N3 13.2(2) . . . .
C1 N1 C8 C7 -169.20(12) . . . .
C1 C2 C3 C4 55.43(19) . . . .
C2 C3 C4 C5 -53.12(19) . . . .
C3 C4 C5 N1 48.55(18) . . . .
C3 C4 C5 C6 170.86(13) . . . .
C4 C5 C6 N2 -170.29(11) . . . .
C5 N1 C1 C2 50.93(18) . . . .
C5 N1 C8 N3 155.76(14) . . . .
C5 N1 C8 C7 -26.68(18) . . . .
C6 N2 C7 N4 176.15(12) . . . .
C6 N2 C7 C8 -4.7(2) . . . .
C7 N2 C6 C5 27.6(2) . . . .
C7 N4 C14 C9 0.0(2) . . . .
C7 N4 C14 C13 -179.63(12) . . . .
C8 N1 C1 C2 -166.29(12) . . . .
C8 N1 C5 C4 170.10(12) . . . .
C8 N1 C5 C6 48.30(17) . . . .
C8 N3 C9 C10 -178.71(13) . . . .
C8 N3 C9 C14 1.5(2) . . . .
C9 N3 C8 N1 176.41(11) . . . .
C9 N3 C8 C7 -1.1(2) . . . .
C9 C10 C11 C12 0.9(2) . . . .
C10 C9 C14 N4 179.24(12) . . . .
C10 C9 C14 C13 -1.2(2) . . . .
C10 C11 C12 O1 178.66(12) . . . .
C10 C11 C12 C13 -0.9(2) . . . .
C11 C12 C13 C14 -0.1(2) . . . .
C12 C13 C14 N4 -179.25(13) . . . .
C12 C13 C14 C9 1.2(2) . . . .
C14 N4 C7 N2 179.60(12) . . . .
C14 N4 C7 C8 0.5(2) . . . .
C14 C9 C10 C11 0.1(2) . . . .
C15 O1 C12 C11 -173.91(13) . . . .
C15 O1 C12 C13 5.7(2) . . . .
