#------------------------------------------------------------------------------
#$Date: 2023-07-05 12:46:19 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284901 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/92/1569272.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_1569272
loop_
_publ_author_name
'Singh, Bara'
'Ansari, Arshad J.'
'Malik, Nirmal'
'Ramasastry, S. S. V.'
_publ_section_title
;
 An interrupted Corey-Chaykovsky reaction of designed azaarenium salts:
 synthesis of complex polycyclic spiro- and fused cyclopropanoids.
;
_journal_issue                   25
_journal_name_full               'Chemical science'
_journal_page_first              6963
_journal_page_last               6969
_journal_paper_doi               10.1039/d3sc01578e
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C22 H19 N O'
_chemical_formula_sum            'C22 H19 N O'
_chemical_formula_weight         311.407
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-01-10 deposited with the CCDC.	2023-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.468(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4984(6)
_cell_length_b                   13.6723(8)
_cell_length_c                   12.6001(8)
_cell_measurement_reflns_used    2118
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.2370
_cell_measurement_theta_min      3.4240
_cell_volume                     1715.44(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      289
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_measured_fraction_theta_max 0.9023
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     14.00  52.10   0.30   25.00    --   29.89  54.00 -30.00  127
  2  ω    -29.00  -2.00   0.30   25.00    --   29.89  54.00  30.00   90
  3  ω    -63.00 117.00   0.30   25.00    --   29.89  54.00-150.00  600
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0626870000
_diffrn_orient_matrix_UB_12      0.0209461000
_diffrn_orient_matrix_UB_13      -0.0305828000
_diffrn_orient_matrix_UB_21      0.0334761000
_diffrn_orient_matrix_UB_22      0.0341590000
_diffrn_orient_matrix_UB_23      -0.0243240000
_diffrn_orient_matrix_UB_31      -0.0052705000
_diffrn_orient_matrix_UB_32      -0.0329719000
_diffrn_orient_matrix_UB_33      -0.0446133000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.9974
_diffrn_reflns_Laue_measured_fraction_max 0.9023
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10342
_diffrn_reflns_point_group_measured_fraction_full 0.9974
_diffrn_reflns_point_group_measured_fraction_max 0.9023
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         32.77
_diffrn_reflns_theta_min         2.53
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       prism
_exptl_crystal_F_000             660.284
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.2820
_refine_diff_density_min         -0.2255
_refine_diff_density_rms         0.0451
_refine_ls_d_res_high            0.6566
_refine_ls_d_res_low             8.0492
_refine_ls_goodness_of_fit_ref   1.1430
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     218
_refine_ls_number_reflns         5728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1430
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1825
_refine_ls_wR_factor_ref         0.2261
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -15
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -9
_reflns_number_gt                3020
_reflns_number_total             5728
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3sc01578e2.cif
_cod_data_source_block           AJA012022
_cod_depositor_comments
'Adding full bibliography for 1569272--1569274.cif.'
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               1569272
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00e,H00g)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00H(H00H), C00I(H00I), C00C(H00C), C009(H009), C00D(H00D),
 C00F(H00F), C008(H008), C00K(H00K), C00O(H00q), C00M(H00M), C00L(H00L),
 C00J(H00J)
2.d Idealised Me refined as rotating group:
 C00N(H00n,H00o,H00p)
;
_olex2_submission_original_sample_id 'AJA 01 202 2'
_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 1.173
_oxdiff_exptl_absorpt_empirical_full_min 0.872
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2
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_refinement_flags_posn
O001 O 0.87814(11) 0.57495(8) 0.64794(9) 0.0825(4) Uani 1.000000 .
C002 C 0.74745(12) 0.80712(10) 0.67322(11) 0.0624(4) Uani 1.000000 .
N003 N 0.70510(16) 1.00557(11) 0.42832(13) 0.0911(5) Uani 1.000000 .
C004 C 0.76419(12) 0.82350(10) 0.55805(11) 0.0629(4) Uani 1.000000 .
C005 C 0.83011(13) 0.65709(11) 0.63380(11) 0.0643(4) Uani 1.000000 .
C006 C 0.78183(12) 0.71320(10) 0.71294(11) 0.0622(4) Uani 1.000000 .
C007 C 0.81363(12) 0.72082(11) 0.53471(11) 0.0639(4) Uani 1.000000 .
C008 C 0.63061(14) 0.85221(12) 0.47316(13) 0.0742(4) Uani 1.000000 .
C009 C 0.86203(15) 0.90526(12) 0.56309(14) 0.0752(4) Uani 1.000000 .
C00A C 0.77107(16) 0.68521(12) 0.81637(12) 0.0748(4) Uani 1.000000 .
C00B C 0.76398(16) 0.67531(12) 0.41764(12) 0.0760(4) Uani 1.000000 .
C00C C 0.70596(16) 0.87494(12) 0.73651(14) 0.0770(4) Uani 1.000000 .
C00D C 0.82966(17) 0.98719(12) 0.50292(14) 0.0806(5) Uani 1.000000 .
C00E C 0.71541(17) 0.57261(12) 0.39536(12) 0.0756(4) Uani 1.000000 .
C00F C 0.60990(18) 0.93485(13) 0.41692(14) 0.0817(5) Uani 1.000000 .
C00G C 0.90601(17) 0.70490(14) 0.46516(15) 0.0880(5) Uani 1.000000 .
C00H C 0.72874(18) 0.75332(14) 0.87772(14) 0.0875(5) Uani 1.000000 .
C00I C 0.69736(18) 0.84752(14) 0.83928(15) 0.0874(5) Uani 1.000000 .
C00J C 0.7940(2) 0.49629(14) 0.37917(14) 0.0933(5) Uani 1.000000 .
C00K C 0.5812(2) 0.55274(16) 0.38255(18) 0.1015(6) Uani 1.000000 .
C00L C 0.7390(3) 0.40432(17) 0.34889(18) 0.1154(7) Uani 1.000000 .
C00M C 0.6064(3) 0.38673(17) 0.33578(18) 0.1201(8) Uani 1.000000 .
C00N C 0.6745(3) 1.09606(15) 0.36601(17) 0.1184(8) Uani 1.000000 .
C00O C 0.5286(3) 0.46079(18) 0.3542(2) 0.1229(8) Uani 1.000000 .
H00A H 0.79212(16) 0.62185(12) 0.84300(12) 0.0898(5) Uiso 1.000000 R
H00H H 0.72103(18) 0.73562(14) 0.94669(14) 0.1049(6) Uiso 1.000000 R
H00I H 0.67027(18) 0.89277(14) 0.88290(15) 0.1049(6) Uiso 1.000000 R
H00C H 0.68410(16) 0.93830(12) 0.71015(14) 0.0924(5) Uiso 1.000000 R
H009 H 0.94965(15) 0.89831(12) 0.61063(14) 0.0902(5) Uiso 1.000000 R
H00D H 0.89569(17) 1.03471(12) 0.51219(14) 0.0968(6) Uiso 1.000000 R
H00F H 0.52500(18) 0.94582(13) 0.36615(14) 0.0980(6) Uiso 1.000000 R
H008 H 0.55927(14) 0.80866(12) 0.46026(13) 0.0890(5) Uiso 1.000000 R
H00K H 0.5263(2) 0.60256(16) 0.39340(18) 0.1218(7) Uiso 1.000000 R
H00q H 0.4391(3) 0.44888(18) 0.3474(2) 0.1475(9) Uiso 1.000000 R
H00M H 0.5698(3) 0.32505(17) 0.31461(18) 0.1442(10) Uiso 1.000000 R
H00L H 0.7927(3) 0.35396(17) 0.33733(18) 0.1385(9) Uiso 1.000000 R
H00J H 0.8845(2) 0.50684(14) 0.38870(14) 0.1119(6) Uiso 1.000000 R
H00B H 0.71130(16) 0.72115(12) 0.36082(12) 0.0913(5) Uiso 1.000000 R
H00e H 0.93508(17) 0.76216(14) 0.43361(15) 0.1056(6) Uiso 1.000000 R
H00g H 0.97271(17) 0.65345(14) 0.48835(15) 0.1056(6) Uiso 1.000000 R
H00n H 0.6349(18) 1.1413(5) 0.4047(8) 0.1776(12) Uiso 1.000000 GR
H00o H 0.7557(4) 1.1235(7) 0.3591(14) 0.1776(12) Uiso 1.000000 GR
H00p H 0.6127(15) 1.0834(3) 0.2929(6) 0.1776(12) Uiso 1.000000 GR
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C006 C002 C004 112.52(13) . . ?
C00C C002 C004 126.92(13) . . ?
C00C C002 C006 120.54(13) . . ?
C00F N003 C00D 116.75(14) . . ?
C00N N003 C00D 121.91(17) . . ?
C00N N003 C00F 121.33(17) . . ?
C007 C004 C002 101.09(10) . . ?
C008 C004 C002 110.29(11) . . ?
C008 C004 C007 112.84(11) . . ?
C009 C004 C002 110.48(12) . . ?
C009 C004 C007 114.43(11) . . ?
C009 C004 C008 107.61(12) . . ?
C006 C005 O001 126.61(13) . . ?
C007 C005 O001 126.47(14) . . ?
C007 C005 C006 106.88(12) . . ?
C005 C006 C002 110.21(12) . . ?
C00A C006 C002 120.19(14) . . ?
C00A C006 C005 129.59(14) . . ?
C005 C007 C004 109.08(11) . . ?
C00B C007 C004 121.06(11) . . ?
C00B C007 C005 118.95(13) . . ?
C00G C007 C004 123.49(13) . . ?
C00G C007 C005 118.43(13) . . ?
C00G C007 C00B 57.97(10) . . ?
C00F C008 C004 123.98(15) . . ?
H008 C008 C004 118.01(8) . . ?
H008 C008 C00F 118.01(10) . . ?
C00D C009 C004 123.47(14) . . ?
H009 C009 C004 118.26(8) . . ?
H009 C009 C00D 118.26(9) . . ?
C00H C00A C006 118.45(15) . . ?
H00A C00A C006 120.78(9) . . ?
H00A C00A C00H 120.78(10) . . ?
C00E C00B C007 123.77(13) . . ?
C00G C00B C007 60.42(10) . . ?
C00G C00B C00E 125.17(15) . . ?
H00B C00B C007 112.63(8) . . ?
H00B C00B C00E 112.63(8) . . ?
H00B C00B C00G 112.63(10) . . ?
C00I C00C C002 119.12(15) . . ?
H00C C00C C002 120.44(9) . . ?
H00C C00C C00I 120.44(10) . . ?
C009 C00D N003 124.01(15) . . ?
H00D C00D N003 118.00(9) . . ?
H00D C00D C009 118.00(10) . . ?
C00J C00E C00B 123.61(16) . . ?
C00K C00E C00B 118.61(15) . . ?
C00K C00E C00J 117.63(17) . . ?
C008 C00F N003 124.16(15) . . ?
H00F C00F N003 117.92(9) . . ?
H00F C00F C008 117.92(10) . . ?
C00B C00G C007 61.61(10) . . ?
H00e C00G C007 117.60(9) . . ?
H00e C00G C00B 117.60(9) . . ?
H00g C00G C007 117.60(9) . . ?
H00g C00G C00B 117.60(10) . . ?
H00g C00G H00e 114.7 . . ?
C00I C00H C00A 121.37(16) . . ?
H00H C00H C00A 119.32(10) . . ?
H00H C00H C00I 119.32(10) . . ?
C00H C00I C00C 120.31(16) . . ?
H00I C00I C00C 119.84(10) . . ?
H00I C00I C00H 119.84(10) . . ?
C00L C00J C00E 120.5(2) . . ?
H00J C00J C00E 119.73(12) . . ?
H00J C00J C00L 119.73(15) . . ?
C00O C00K C00E 121.2(2) . . ?
H00K C00K C00E 119.42(11) . . ?
H00K C00K C00O 119.42(15) . . ?
C00M C00L C00J 120.8(2) . . ?
H00L C00L C00J 119.62(15) . . ?
H00L C00L C00M 119.62(14) . . ?
C00O C00M C00L 119.3(2) . . ?
H00M C00M C00L 120.37(14) . . ?
H00M C00M C00O 120.37(15) . . ?
H00n C00N N003 109.5 . . ?
H00o C00N N003 109.5 . . ?
H00o C00N H00n 109.5 . . ?
H00p C00N N003 109.5 . . ?
H00p C00N H00n 109.5 . . ?
H00p C00N H00o 109.5 . . ?
C00M C00O C00K 120.6(2) . . ?
H00q C00O C00K 119.69(15) . . ?
H00q C00O C00M 119.69(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
O001 C005 1.2208(18) . ?
C002 C004 1.5324(19) . ?
C002 C006 1.384(2) . ?
C002 C00C 1.380(2) . ?
N003 C00D 1.370(2) . ?
N003 C00F 1.365(2) . ?
N003 C00N 1.446(2) . ?
C004 C007 1.557(2) . ?
C004 C008 1.5213(19) . ?
C004 C009 1.506(2) . ?
C005 C006 1.470(2) . ?
C005 C007 1.4870(19) . ?
C006 C00A 1.397(2) . ?
C007 C00B 1.532(2) . ?
C007 C00G 1.515(2) . ?
C008 C00F 1.315(2) . ?
C008 H008 0.9300 . ?
C009 C00D 1.335(2) . ?
C009 H009 0.9300 . ?
C00A C00H 1.371(2) . ?
C00A H00A 0.9300 . ?
C00B C00E 1.490(2) . ?
C00B C00G 1.476(2) . ?
C00B H00B 0.9800 . ?
C00C C00I 1.378(2) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00E C00J 1.385(2) . ?
C00E C00K 1.393(3) . ?
C00F H00F 0.9300 . ?
C00G H00e 0.9700 . ?
C00G H00g 0.9700 . ?
C00H C00I 1.379(3) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00J C00L 1.386(3) . ?
C00J H00J 0.9300 . ?
C00K C00O 1.374(3) . ?
C00K H00K 0.9300 . ?
C00L C00M 1.370(3) . ?
C00L H00L 0.9300 . ?
C00M C00O 1.366(3) . ?
C00M H00M 0.9300 . ?
C00N H00n 0.9600 . ?
C00N H00o 0.9600 . ?
C00N H00p 0.9600 . ?
C00O H00q 0.9300 . ?
