#------------------------------------------------------------------------------
#$Date: 2023-03-21 03:18:43 +0200 (Tue, 21 Mar 2023) $
#$Revision: 281951 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/23/7062383.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_7062383
loop_
_publ_author_name
'Guo, Hao'
'Wang, Huahao'
'Zhao, Hongyi'
'Zhang, Dongfeng'
_publ_section_title
;
 Visible light-promoted synthesis of
 4,6a-dihydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-diones via [3+2]
 cycloaddition reaction of 2H-azirines with maleimides
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5634
_journal_page_last               5638
_journal_paper_doi               10.1039/D2NJ06257G
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C19 H16 N2 O2'
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.34
_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
_audit_creation_date             2020-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-11-30 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                109.529(3)
_cell_angle_beta                 106.432(2)
_cell_angle_gamma                96.016(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9663(2)
_cell_length_b                   9.2196(3)
_cell_length_c                   10.1384(3)
_cell_measurement_reflns_used    10071
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      31.1820
_cell_measurement_theta_min      2.2190
_cell_volume                     738.97(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_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      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.817
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00  55.00   0.50    3.00    --    5.00  45.00  60.00   56
  2  ω    -30.00  -4.00   0.50    3.00    --    5.00  45.00  60.00   52
  3  ω    -79.00  93.00   0.50    3.00    --    5.00  45.00 150.00  344
  4  ω     -3.00  56.00   0.50    3.00    --   -8.00  45.00   0.00  118
  5  ω    -82.00 -32.00   0.50    3.00    --   -8.00  45.00   0.00  100
  6  ω    -97.00  80.00   0.50    3.00    --   -8.00  45.00  90.00  354
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0088026000
_diffrn_orient_matrix_UB_12      -0.0438819000
_diffrn_orient_matrix_UB_13      -0.0685875000
_diffrn_orient_matrix_UB_21      -0.0074278000
_diffrn_orient_matrix_UB_22      0.0650896000
_diffrn_orient_matrix_UB_23      -0.0219191000
_diffrn_orient_matrix_UB_31      0.0837699000
_diffrn_orient_matrix_UB_32      0.0290139000
_diffrn_orient_matrix_UB_33      0.0322803000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.817
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13059
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.331
_diffrn_reflns_theta_min         2.266
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
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    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0402
_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/[σ²(Fo²)+(0.0643P)²+0.2238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1161
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3692
_reflns_number_total             3958
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj06257g2.cif
_cod_data_source_block           mx8663
_cod_database_code               7062383
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_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 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_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 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.830
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 0.53510(10) 0.39569(9) 0.09942(9) 0.03137(19) Uani 1 1 d . . . . .
O2 O 0.80859(10) 0.79732(11) 0.54339(9) 0.0354(2) Uani 1 1 d . . . . .
N1 N 0.69820(10) 0.57845(11) 0.32626(10) 0.02411(18) Uani 1 1 d . . . . .
N2 N 0.30048(10) 0.56228(9) 0.39071(9) 0.02253(18) Uani 1 1 d . . . . .
C1 C 0.55681(11) 0.51341(11) 0.20717(11) 0.02144(19) Uani 1 1 d . . . . .
C2 C 0.43831(11) 0.61576(11) 0.23934(10) 0.01875(18) Uani 1 1 d . . . . .
H2 H 0.404255 0.663711 0.166048 0.023 Uiso 1 1 calc R . . . .
C3 C 0.52582(11) 0.73883(11) 0.39622(10) 0.02038(19) Uani 1 1 d . . . . .
H3 H 0.520023 0.846485 0.402860 0.024 Uiso 1 1 calc R . . . .
C4 C 0.69486(12) 0.71640(12) 0.43511(11) 0.0242(2) Uani 1 1 d . . . . .
C5 C 0.29804(11) 0.52482(10) 0.25660(10) 0.01927(18) Uani 1 1 d . . . . .
C6 C 0.44185(12) 0.68648(11) 0.49442(10) 0.02072(19) Uani 1 1 d . . . . .
H6 H 0.514285 0.638988 0.551087 0.025 Uiso 1 1 calc R . . . .
C7 C 0.83433(13) 0.50475(16) 0.33915(14) 0.0334(3) Uani 1 1 d . . . . .
H7A H 0.820962 0.427014 0.380974 0.050 Uiso 1 1 calc GR . . . .
H7B H 0.929921 0.583576 0.402607 0.050 Uiso 1 1 calc GR . . . .
H7C H 0.842031 0.454951 0.242404 0.050 Uiso 1 1 calc GR . . . .
C8 C 0.17102(11) 0.40129(11) 0.12923(10) 0.01978(19) Uani 1 1 d . . . . .
C9 C 0.14970(12) 0.39018(12) -0.01561(11) 0.0249(2) Uani 1 1 d . . . . .
H9 H 0.217659 0.459702 -0.032764 0.030 Uiso 1 1 calc R . . . .
C10 C 0.02723(13) 0.27557(14) -0.13469(12) 0.0302(2) Uani 1 1 d . . . . .
H10 H 0.013263 0.269351 -0.231028 0.036 Uiso 1 1 calc R . . . .
C11 C -0.07372(14) 0.17099(14) -0.11082(13) 0.0339(3) Uani 1 1 d . . . . .
H11 H -0.155224 0.094259 -0.190809 0.041 Uiso 1 1 calc R . . . .
C12 C -0.05311(14) 0.18081(14) 0.03274(14) 0.0331(2) Uani 1 1 d . . . . .
H12 H -0.121214 0.110509 0.048942 0.040 Uiso 1 1 calc R . . . .
C13 C 0.06853(12) 0.29487(12) 0.15273(12) 0.0259(2) Uani 1 1 d . . . . .
H13 H 0.081825 0.300473 0.248797 0.031 Uiso 1 1 calc R . . . .
C14 C 0.40150(12) 0.81952(11) 0.60389(10) 0.02014(19) Uani 1 1 d . . . . .
C15 C 0.51787(12) 0.91031(12) 0.74111(11) 0.0240(2) Uani 1 1 d . . . . .
H15 H 0.618426 0.887552 0.764288 0.029 Uiso 1 1 calc R . . . .
C16 C 0.48472(13) 1.03447(12) 0.84346(11) 0.0267(2) Uani 1 1 d . . . . .
H16 H 0.563776 1.096307 0.933774 0.032 Uiso 1 1 calc R . . . .
C17 C 0.33401(14) 1.06624(12) 0.81110(12) 0.0286(2) Uani 1 1 d . . . . .
H17 H 0.311234 1.148370 0.880229 0.034 Uiso 1 1 calc R . . . .
C18 C 0.21714(13) 0.97549(13) 0.67554(13) 0.0315(2) Uani 1 1 d . . . . .
H18 H 0.115597 0.996194 0.654047 0.038 Uiso 1 1 calc R . . . .
C19 C 0.25141(13) 0.85356(12) 0.57161(12) 0.0273(2) Uani 1 1 d . . . . .
H19 H 0.173278 0.794448 0.479910 0.033 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 0.0033 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
_geom_angle_publ_flag
C1 N1 C4 113.64(8) . . ?
C1 N1 C7 123.01(9) . . ?
C4 N1 C7 123.28(9) . . ?
C5 N2 C6 110.83(8) . . ?
O1 C1 N1 124.51(9) . . ?
O1 C1 C2 127.66(9) . . ?
N1 C1 C2 107.83(8) . . ?
C1 C2 C3 104.54(7) . . ?
C5 C2 C1 111.16(7) . . ?
C5 C2 C3 103.30(7) . . ?
C2 C3 C6 103.79(7) . . ?
C4 C3 C2 105.33(8) . . ?
C4 C3 C6 109.72(8) . . ?
O2 C4 N1 124.31(10) . . ?
O2 C4 C3 127.91(10) . . ?
N1 C4 C3 107.72(8) . . ?
N2 C5 C2 114.64(8) . . ?
N2 C5 C8 122.64(9) . . ?
C8 C5 C2 122.70(8) . . ?
N2 C6 C3 106.38(7) . . ?
N2 C6 C14 112.45(8) . . ?
C14 C6 C3 114.27(7) . . ?
C9 C8 C5 120.72(9) . . ?
C9 C8 C13 119.05(9) . . ?
C13 C8 C5 120.22(9) . . ?
C10 C9 C8 120.27(10) . . ?
C11 C10 C9 120.43(10) . . ?
C10 C11 C12 119.70(10) . . ?
C11 C12 C13 120.48(10) . . ?
C12 C13 C8 120.06(10) . . ?
C15 C14 C6 119.16(9) . . ?
C19 C14 C6 121.71(9) . . ?
C19 C14 C15 119.13(9) . . ?
C16 C15 C14 120.45(10) . . ?
C17 C16 C15 120.00(9) . . ?
C16 C17 C18 119.89(10) . . ?
C17 C18 C19 120.11(10) . . ?
C14 C19 C18 120.38(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
O1 C1 1.2050(12) . ?
O2 C4 1.2088(13) . ?
N1 C1 1.3839(13) . ?
N1 C4 1.3873(14) . ?
N1 C7 1.4531(13) . ?
N2 C5 1.2791(12) . ?
N2 C6 1.4698(12) . ?
C1 C2 1.5251(13) . ?
C2 C3 1.5276(12) . ?
C2 C5 1.5222(13) . ?
C3 C4 1.5092(14) . ?
C3 C6 1.5685(13) . ?
C5 C8 1.4746(13) . ?
C6 C14 1.5091(13) . ?
C8 C9 1.3929(14) . ?
C8 C13 1.3982(14) . ?
C9 C10 1.3906(14) . ?
C10 C11 1.3800(17) . ?
C11 C12 1.3846(18) . ?
C12 C13 1.3889(15) . ?
C14 C15 1.3936(13) . ?
C14 C19 1.3872(14) . ?
C15 C16 1.3882(14) . ?
C16 C17 1.3842(16) . ?
C17 C18 1.3855(16) . ?
C18 C19 1.3900(15) . ?
