Crystal structure of N-(4-methoxybenzyl)pyridazin-3-amine- a rare Z′ = 4 structure, C12H13N3O
Lou, Xin-Hua; Zhou, Qing-Li; Liu, Wen-Yuan; Hu, Xue-Qing; Zeitschrift für Kristallographie - New Crystal Structures 234 (2018) 105–107; doi:10.1515/ncrs-2018-0212

data_8105557
_publ_section_title
;
 Crystal structure of N-(4-methoxybenzyl)pyridazin-3-amine- a rare
 Z&#x2032; = 4 structure, C12H13N3O
;
_journal_issue                   1
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              105
_journal_page_last               107
_journal_paper_doi               10.1515/ncrs-2018-0212
_journal_volume                  234
_journal_year                    2018
_chemical_formula_moiety         'C12 H13 N3 O'
_chemical_formula_sum            'C12 H13 N3 O'
_chemical_formula_weight         215.25
_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     direct
_audit_creation_date             2015-05-07
_audit_creation_method           ' '
_cell_angle_alpha                86.607(7)
_cell_angle_beta                 88.529(7)
_cell_angle_gamma                62.515(9)
_cell_formula_units_Z            8
_cell_length_a                   10.2233(9)
_cell_length_b                   10.2902(9)
_cell_length_c                   24.2253(19)
_cell_measurement_reflns_used    4916
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.6180
_cell_measurement_theta_min      4.8730
_cell_volume                     2256.9(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -10.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 37

  2 omega   36.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 32

  3 omega   -3.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   30.0000 43

  4 omega  -68.00  -42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -120.0000 26

  5 omega  -64.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  120.0000 29

  6 omega  -12.00   77.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  120.0000 89

  7 omega   19.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000    0.0000 70

  8 omega   -4.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000   30.0000 98

  9 omega   16.00   58.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000 -150.0000 42

 10 omega   49.00  126.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000   60.0000 77

 11 omega   18.00   67.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -19.0000   90.0000 49

 12 omega   72.00  113.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -150.0000 41

 13 omega   63.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -60.0000 53

 14 omega   71.00   97.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 26

 15 omega   96.00  167.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -150.0000 71

 16 omega   51.00  107.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -101.0000   32.0000 56

 17 omega   61.00  112.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 51

 18 omega  122.00  172.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -180.0000 50

 19 omega   44.00  104.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -60.0000 60

 20 omega   42.00   92.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 50

 21 omega   52.00   89.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 37

 22 omega   51.00   84.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 33

 23 omega   47.00   81.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  120.0000 34

 24 omega   93.00  160.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -120.0000 67

 25 omega   42.00   91.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 49

 26 omega   41.00   89.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 48

 27 omega   62.00  176.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000    0.0000 114

 28 omega   42.00   94.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 52

 29 omega   55.00  108.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -150.0000 53

 30 omega  -30.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000    0.0000 100

 31 omega   -4.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   90.0000 46

 32 omega  -69.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -150.0000 90

 33 omega   35.00  125.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  150.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1494036000
_diffrn_orient_matrix_UB_12      -0.1389901000
_diffrn_orient_matrix_UB_13      0.0060386000
_diffrn_orient_matrix_UB_21      -0.0375360000
_diffrn_orient_matrix_UB_22      -0.0250050000
_diffrn_orient_matrix_UB_23      0.0604406000
_diffrn_orient_matrix_UB_31      -0.0714510000
_diffrn_orient_matrix_UB_32      -0.0927328000
_diffrn_orient_matrix_UB_33      -0.0191970000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16086
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.103
_diffrn_reflns_theta_max         67.103
_diffrn_reflns_theta_min         3.656
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description
;
;
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.026
_refine_ls_extinction_coef       0.00140(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     582
_refine_ls_number_reflns         8063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0533P)^2^+0.2095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1239
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6060
_reflns_number_total             8063
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2018-0212_suppl.cif
_cod_data_source_block           2
_cod_database_code               8105557
_chemical_oxdiff_formula         C20H20N4O4P1
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.865
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C5B(H5BA,H5BB), C5A(H5AA,H5AB), C5C(H5CA,H5CB)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C10(H10), C11(H11), N3(H3A), C1B(H1B),
  C2B(H2B), C3B(H3B), C7B(H7B), C8B(H8B), C10B(H10B), C11B(H11B), N3B(H3BA),
 C1A(H1A), C2A(H2A), C3A(H3AA), C7A(H7A), C8A(H8A), C10A(H10A), C11A(H11A),
 N3A(H3AB), C1C(H1C), C2C(H2C), C3C(H3C), C7C(H7C), C8C(H8C), C10C(H10C),
 C11C(H11C), N3C(H3CA)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C12B(H12D,H12E,H12F), C12A(H12G,H12H,H12I), C12C(H12J,
 H12K,H12L)
;