#------------------------------------------------------------------------------
#$Date: 2020-06-19 02:12:45 +0300 (Fri, 19 Jun 2020) $
#$Revision: 253256 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038501.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_4038501
loop_
_publ_author_name
'Kumar, Neha'
'Agrawal, Abhijeet R.'
'Choudhury, Aditya'
'Zade, Sanjio S.'
_publ_section_title
;
 The Effect of Base and Nucleophile on the Nucleophilic Substitution of
 Methoxytropone Derivatives: An Easy Access to 4- and 5-Substituted
 Multifunctional Azulenes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00951
_journal_year                    2020
_chemical_formula_moiety         '0.11(C15 H13 N3)'
_chemical_formula_sum            'C1.714 H1.486 N0.343'
_chemical_formula_weight         26.89
_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     iterative
_audit_creation_date             2019-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.001(14)
_cell_angle_gamma                90
_cell_formula_units_Z            35
_cell_length_a                   7.0220(11)
_cell_length_b                   11.2016(17)
_cell_length_c                   15.789(2)
_cell_measurement_reflns_used    2412
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      65.9630
_cell_measurement_theta_min      4.7800
_cell_volume                     1226.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9999
_diffrn_measured_fraction_theta_max 0.9999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -14.00 100.00   1.00    2.00    --   24.08  57.00  30.00  114
  2  ω    -14.00 100.00   1.00    2.00    --   24.08  57.00 -60.00  114
  3  ω      1.00  79.00   1.00    2.00    --   24.08 -99.00   0.00   78
  4  ω     -4.00 108.00   1.00    8.00    --   66.04 -94.00-180.00  112
  5  ω     19.00 146.00   1.00    8.00    --   66.04  45.00 -60.00  127
  6  ω    100.00 153.00   1.00    8.00    --   66.04  87.00 -54.00   53
  7  ω     29.00 143.00   1.00    8.00    --   66.04  61.00-120.00  114
  8  ω     57.00 150.00   1.00    8.00    --   66.04 178.00-180.00   93
  9  ω    100.00 151.00   1.00    8.00    --   66.04 111.00 150.00   51
 10  ω     21.00 113.00   1.00   16.00    --  108.00-104.00-180.00   92
 11  ω    101.00 178.00   1.00   16.00    --  108.00 104.00 -30.00   77
 12  ω    101.00 178.00   1.00   16.00    --  108.00 104.00-150.00   77
 13  ω     31.00 147.00   1.00   16.00    --  108.00 -54.00 150.00  116
 14  ω     99.00 178.00   1.00   16.00    --  108.00  87.00 -54.00   79
 15  ω     71.00 178.00   1.00   16.00    --  108.00  65.00  60.00  107
 16  ω     70.00 178.00   1.00   16.00    --  108.00  67.00-129.88  108
 17  ω     65.00 178.00   1.00   16.00    --  108.00  77.00-120.00  113
 18  ω     26.00 120.00   1.00   16.00    --  108.00-123.00  49.59   94
 19  ω     71.00 178.00   1.00   16.00    --  108.00  65.00 -60.00  107
 20  ω     21.00 113.00   1.00   16.00    --  108.00-104.00  60.00   92
 21  ω     69.00 178.00   1.00   16.00    --  108.00  54.00 -90.00  109
 22  ω    -19.00 109.00   1.00    2.00    --   24.08  77.00-120.00  128
 23  ω    -63.00 108.00   1.00    2.00    --   24.08 -19.00-120.00  171
 24  ω    -14.00 100.00   1.00    2.00    --   24.08  57.00 150.00  114
 25  ω     57.00 118.00   1.00    2.00    --   24.08 178.00 -90.00   61
 26  ω     29.00 143.00   1.00    8.00    --   66.04  61.00  30.00  114
 27  ω     29.00 143.00   1.00    8.00    --   66.04  61.00-180.00  114
 28  ω     29.00 143.00   1.00    8.00    --   66.04  61.00 120.00  114
 29  ω     23.00 151.00   1.00    8.00    --   66.04  77.00 -30.00  128
 30  ω     23.00  84.00   1.00    8.00    --   66.04  77.00  60.00   61
 31  ω    100.00 151.00   1.00    8.00    --   66.04 111.00  60.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0952684000
_diffrn_orient_matrix_UB_12      -0.1174820000
_diffrn_orient_matrix_UB_13      0.0352407000
_diffrn_orient_matrix_UB_21      0.0961556000
_diffrn_orient_matrix_UB_22      0.0656744000
_diffrn_orient_matrix_UB_23      0.0812779000
_diffrn_orient_matrix_UB_31      -0.1762613000
_diffrn_orient_matrix_UB_32      -0.0276191000
_diffrn_orient_matrix_UB_33      0.0438335000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0878
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8024
_diffrn_reflns_theta_full        66.3872
_diffrn_reflns_theta_max         66.39
_diffrn_reflns_theta_min         5.67
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.2740
_exptl_crystal_description       block
_exptl_crystal_F_000             497.4284
_refine_diff_density_max         0.5580
_refine_diff_density_min         -0.5326
_refine_diff_density_rms         0.1379
_refine_ls_d_res_high            0.8414
_refine_ls_d_res_low             7.7973
_refine_ls_goodness_of_fit_ref   1.1139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1139
_refine_ls_R_factor_all          0.1379
_refine_ls_R_factor_gt           0.0821
_refine_ls_shift/su_max          0.0014
_refine_ls_shift/su_mean         0.0003
_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          0.1705
_refine_ls_wR_factor_ref         0.1987
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -8
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -6
_reflns_number_gt                1199
_reflns_number_total             1822
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo0c00951_si_002.cif
_cod_data_source_block           CNPRAZ_100K
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038501
_chemical_oxdiff_formula         'C H N'
_reflns_odcompleteness_completeness 97.24
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N001(H00a,H00b)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00g,H00h), C00H(H00i,H00j)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F)
2.d Idealised Me refined as rotating group:
 C00I(H00k,H00l,H00m)
;
_olex2_date_sample_data_collection 2019-09-04
_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 1.910
_oxdiff_exptl_absorpt_empirical_full_min 0.322
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
N001 N 0.1894(4) 0.5713(3) 0.27192(17) 0.0448(8) Uani 1.000000 .
H00a H 0.185(4) 0.5009(3) 0.25006(18) 0.0538(9) Uiso 1.000000 GR
H00b H 0.084(2) 0.609(2) 0.2537(2) 0.0538(9) Uiso 1.000000 GR
N002 N 0.2476(5) 0.8704(3) 0.35265(19) 0.0604(10) Uani 1.000000 .
C003 C 0.2137(4) 0.5621(3) 0.35817(19) 0.0368(8) Uani 1.000000 .
N004 N 0.1456(5) 0.2536(3) 0.3361(2) 0.0544(9) Uani 1.000000 .
C005 C 0.2038(5) 0.4583(3) 0.4071(2) 0.0390(8) Uani 1.000000 .
C006 C 0.2426(4) 0.4858(3) 0.4953(2) 0.0400(9) Uani 1.000000 .
C007 C 0.2491(5) 0.6594(3) 0.4167(2) 0.0403(9) Uani 1.000000 .
C008 C 0.2553(5) 0.7782(3) 0.3856(2) 0.0453(9) Uani 1.000000 .
C009 C 0.1724(5) 0.3456(3) 0.3701(2) 0.0419(9) Uani 1.000000 .
C00A C 0.2757(5) 0.6150(3) 0.5026(2) 0.0419(9) Uani 1.000000 .
C00B C 0.3286(5) 0.6813(3) 0.5778(2) 0.0442(9) Uani 1.000000 .
C00C C 0.2483(5) 0.4004(3) 0.5599(2) 0.0470(9) Uani 1.000000 .
H00C H 0.2240(5) 0.3222(3) 0.5415(2) 0.0564(11) Uiso 1.000000 R
C00D C 0.3295(5) 0.5211(4) 0.6919(2) 0.0542(11) Uani 1.000000 .
H00D H 0.3480(5) 0.5140(4) 0.7513(2) 0.0651(13) Uiso 1.000000 R
C00E C 0.2854(6) 0.4170(4) 0.6475(2) 0.0520(10) Uani 1.000000 .
H00E H 0.2798(6) 0.3488(4) 0.6807(2) 0.0624(12) Uiso 1.000000 R
C00F C 0.3503(5) 0.6346(4) 0.6612(2) 0.0511(10) Uani 1.000000 .
H00F H 0.3855(5) 0.6911(4) 0.7040(2) 0.0613(12) Uiso 1.000000 R
C00G C 0.3737(5) 0.8126(3) 0.5729(2) 0.0490(10) Uani 1.000000 .
H00g H 0.4754(5) 0.8327(3) 0.6197(2) 0.0588(11) Uiso 1.000000 R
H00h H 0.4216(5) 0.8281(3) 0.5196(2) 0.0588(11) Uiso 1.000000 R
C00H C 0.2051(6) 0.8914(4) 0.5775(3) 0.0547(11) Uani 1.000000 .
H00i H 0.1025(6) 0.8709(4) 0.5312(3) 0.0657(13) Uiso 1.000000 R
H00j H 0.1582(6) 0.8771(4) 0.6312(3) 0.0657(13) Uiso 1.000000 R
C00I C 0.2535(6) 1.0228(4) 0.5712(3) 0.0667(12) Uani 1.000000 .
H00k H 0.294(5) 1.0381(7) 0.5170(9) 0.1000(19) Uiso 1.000000 GR
H00l H 0.1414(15) 1.0699(4) 0.576(2) 0.1000(19) Uiso 1.000000 GR
H00m H 0.355(3) 1.0435(8) 0.6167(13) 0.1000(19) 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 0.01920 0.00962 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'
N 0.03256 0.01839 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
H00b N001 H00a 109.5 . . ?
C003 N001 H00a 109.0 . . ?
C003 N001 H00b 109.9 . . ?
C005 C003 N001 127.5(3) . . ?
C007 C003 N001 125.3(3) . . ?
C007 C003 C005 107.2(3) . . ?
C006 C005 C003 110.1(3) . . ?
C009 C005 C003 122.5(3) . . ?
C009 C005 C006 127.3(3) . . ?
C00A C006 C005 107.2(3) . . ?
C00C C006 C005 123.4(3) . . ?
C00C C006 C00A 129.4(3) . . ?
C008 C007 C003 120.3(3) . . ?
C00A C007 C003 109.4(3) . . ?
C00A C007 C008 130.3(3) . . ?
C007 C008 N002 172.6(4) . . ?
C005 C009 N004 177.4(4) . . ?
C007 C00A C006 105.9(3) . . ?
C00B C00A C006 127.3(3) . . ?
C00B C00A C007 126.7(3) . . ?
C00F C00B C00A 125.0(4) . . ?
C00G C00B C00A 120.2(3) . . ?
C00G C00B C00F 114.7(3) . . ?
H00C C00C C006 115.8(2) . . ?
C00E C00C C006 128.3(4) . . ?
C00E C00C H00C 115.8(2) . . ?
C00E C00D H00D 115.3(2) . . ?
C00F C00D H00D 115.3(2) . . ?
C00F C00D C00E 129.4(3) . . ?
C00D C00E C00C 128.2(3) . . ?
H00E C00E C00C 115.9(2) . . ?
H00E C00E C00D 115.9(2) . . ?
C00D C00F C00B 132.3(4) . . ?
H00F C00F C00B 113.9(2) . . ?
H00F C00F C00D 113.9(2) . . ?
H00g C00G C00B 108.83(18) . . ?
H00h C00G C00B 108.8(2) . . ?
H00h C00G H00g 107.7 . . ?
C00H C00G C00B 113.6(3) . . ?
C00H C00G H00g 108.8(2) . . ?
C00H C00G H00h 108.8(2) . . ?
H00i C00H C00G 109.1(2) . . ?
H00j C00H C00G 109.1(2) . . ?
H00j C00H H00i 107.8 . . ?
C00I C00H C00G 112.6(3) . . ?
C00I C00H H00i 109.1(2) . . ?
C00I C00H H00j 109.1(2) . . ?
H00k C00I C00H 109.5 . . ?
H00l C00I C00H 109.5 . . ?
H00l C00I H00k 109.5 . . ?
H00m C00I C00H 109.5 . . ?
H00m C00I H00k 109.5 . . ?
H00m C00I H00l 109.5 . . ?
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 H00a 0.8601 . ?
N001 H00b 0.8599 . ?
N001 C003 1.350(4) . ?
N002 C008 1.154(4) . ?
C003 C005 1.404(5) . ?
C003 C007 1.425(5) . ?
N004 C009 1.163(5) . ?
C005 C006 1.411(5) . ?
C005 C009 1.394(5) . ?
C006 C00A 1.467(5) . ?
C006 C00C 1.394(5) . ?
C007 C008 1.421(5) . ?
C007 C00A 1.429(5) . ?
C00A C00B 1.401(5) . ?
C00B C00F 1.404(5) . ?
C00B C00G 1.509(5) . ?
C00C H00C 0.9300 . ?
C00C C00E 1.380(5) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.371(6) . ?
C00D C00F 1.376(6) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00G H00g 0.9700 . ?
C00G H00h 0.9700 . ?
C00G C00H 1.487(5) . ?
C00H H00i 0.9700 . ?
C00H H00j 0.9700 . ?
C00H C00I 1.518(6) . ?
C00I H00k 0.9600 . ?
C00I H00l 0.9600 . ?
C00I H00m 0.9600 . ?
