#------------------------------------------------------------------------------
#$Date: 2019-11-24 02:34:36 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236282 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/75/4037529.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_4037529
loop_
_publ_author_name
'Miao, Maozhong'
'Luo, Yi'
'Xu, Huaping'
'Jin, Mengchao'
'Chen, Zhengkai'
'Xu, Jianfeng'
'Ren, Hongjun'
_publ_section_title
;
 Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the
 Application for the Synthesis of Pyrroles.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12224
_journal_page_last               12237
_journal_paper_doi               10.1021/acs.joc.7b02087
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_Int_Tables_number      5
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-07-07
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.06.07 svn.r3419 for OlexSys, GUI svn.r5356)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.790(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5394(7)
_cell_length_b                   5.6134(2)
_cell_length_c                   19.1987(10)
_cell_measurement_reflns_used    1208
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2180
_cell_measurement_theta_min      4.7800
_cell_volume                     1389.37(12)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.6674
_diffrn_measured_fraction_theta_max 0.6674
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     24.00  82.00   1.00    2.95    --   36.71  57.00  30.00   58
  2  ω     13.00 104.00   1.00    2.95    --   36.71  77.00 -90.00   91
  3  ω     70.00 103.00   1.00    2.95    --   36.71  77.00-150.00   33
  4  ω     94.00 169.00   1.00   11.81    --  108.00  45.00 -30.00   75
  5  ω    102.00 161.00   1.00   11.81    --  108.00  45.00  90.00   59
  6  ω     61.00  96.00   1.00    2.95    --   36.71 178.00  90.00   35
  7  ω     28.00  55.00   1.00    2.95    --   36.71  77.00-150.00   27
  8  ω     54.00 134.00   1.00   11.81    --  108.00 -15.00 -60.00   80
  9  ω     91.00 121.00   1.00   11.81    --  108.00-130.00   3.00   30
 10  ω     59.00  87.00   1.00   11.81    --  108.00-130.00   3.00   28
 11  ω     41.00 109.00   1.00   11.81    --  108.00 -95.00   0.00   68
 12  ω     44.00 124.00   1.00   11.81    --  108.00 -61.00   0.00   80
 13  ω     10.00  70.00   1.00    2.95    --   36.71 -99.00-180.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0986414000
_diffrn_orient_matrix_UB_12      0.0422377000
_diffrn_orient_matrix_UB_13      -0.0648876000
_diffrn_orient_matrix_UB_21      0.0609209000
_diffrn_orient_matrix_UB_22      -0.0575432000
_diffrn_orient_matrix_UB_23      -0.0537845000
_diffrn_orient_matrix_UB_31      -0.0289967000
_diffrn_orient_matrix_UB_32      -0.2649916000
_diffrn_orient_matrix_UB_33      0.0013113000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            2434
_diffrn_reflns_theta_full        72.2334
_diffrn_reflns_theta_max         72.23
_diffrn_reflns_theta_min         3.54
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73574
_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_density_diffrn    1.2636
_exptl_crystal_F_000             561.7372
_refine_diff_density_max         0.1110
_refine_diff_density_min         -0.1256
_refine_diff_density_rms         0.0290
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_d_res_high            0.8095
_refine_ls_d_res_low             12.4841
_refine_ls_goodness_of_fit_ref   1.0305
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1822
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0305
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0666P)²+0.0781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.282
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              4
_reflns_limit_k_min              -6
_reflns_limit_l_max              23
_reflns_limit_l_min              -23
_reflns_number_gt                1707
_reflns_number_total             1822
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo7b02087_si_001.cif
_cod_data_source_block           20170706-1_cmpd_6a_prime
_cod_original_sg_symbol_Hall     ' C 2y (x,y,-x+z)'
_cod_database_code               4037529
_chemical_oxdiff_formula         'C H O'
_reflns_odcompleteness_completeness 99.71
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18a,H18b), C17(H17a,H17b)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C2(H2), C6(H6), C3(H3), C5(H5), C4(H4), C15(H15), C14(H14),
 C12(H12), C13(H13)
;
_olex2_date_sample_data_collection 2017-07-06
_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 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.576
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z
3 x+1/2,y+1/2,z+1/2
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
O9 O 0.02515(14) 0.0314(3) 0.38806(10) 0.0692(5) Uani 1.000000 .
O20 O -0.14198(15) 0.7456(4) 0.23004(10) 0.0752(6) Uani 1.000000 .
C10 C 0.18464(14) 0.2182(4) 0.44463(10) 0.0391(4) Uani 1.000000 .
C8 C 0.07663(15) 0.2100(4) 0.39272(10) 0.0420(4) Uani 1.000000 .
C1 C 0.06680(12) 0.4210(4) 0.27662(10) 0.0390(4) Uani 1.000000 .
C11 C 0.25187(15) 0.4061(4) 0.44642(11) 0.0480(4) Uani 1.000000 .
H11 H 0.23066(15) 0.5323(4) 0.41388(11) 0.0576(5) Uiso 1.000000 R
C2 C 0.03991(16) 0.2319(4) 0.22794(12) 0.0484(5) Uani 1.000000 .
H2 H 0.00099(16) 0.1060(4) 0.23713(12) 0.0581(6) Uiso 1.000000 R
C6 C 0.12434(15) 0.6068(4) 0.26149(12) 0.0456(4) Uani 1.000000 .
H6 H 0.14198(15) 0.7355(4) 0.29339(12) 0.0547(5) Uiso 1.000000 R
C19 C -0.14140(15) 0.6501(4) 0.28570(12) 0.0477(5) Uani 1.000000 .
C3 C 0.07131(19) 0.2307(5) 0.16531(12) 0.0562(6) Uani 1.000000 .
H3 H 0.05325(19) 0.1036(5) 0.13281(12) 0.0675(7) Uiso 1.000000 R
C5 C 0.15597(16) 0.6029(5) 0.19923(13) 0.0537(5) Uani 1.000000 .
H5 H 0.19568(16) 0.7274(5) 0.19016(13) 0.0645(6) Uiso 1.000000 R
C4 C 0.12895(17) 0.4164(5) 0.15104(12) 0.0563(5) Uani 1.000000 .
H4 H 0.14936(17) 0.4152(5) 0.10898(12) 0.0675(7) Uiso 1.000000 R
C7 C 0.03277(13) 0.4274(4) 0.34527(10) 0.0395(4) Uani 1.000000 .
H7 H 0.06172(13) 0.5710(4) 0.37306(10) 0.0474(5) Uiso 1.000000 R
C15 C 0.21808(17) 0.0315(4) 0.49363(11) 0.0492(5) Uani 1.000000 .
H15 H 0.17405(17) -0.0963(4) 0.49290(11) 0.0591(6) Uiso 1.000000 R
C16 C -0.08534(14) 0.4345(4) 0.32800(11) 0.0452(4) Uani 1.000000 .
H16 H -0.11697(14) 0.2857(4) 0.30503(11) 0.0542(5) Uiso 1.000000 R
C14 C 0.31625(19) 0.0344(5) 0.54339(13) 0.0609(6) Uani 1.000000 .
H14 H 0.33782(19) -0.0913(5) 0.57607(13) 0.0730(7) Uiso 1.000000 R
C12 C 0.35093(17) 0.4070(5) 0.49664(14) 0.0620(6) Uani 1.000000 .
H12 H 0.39580(17) 0.5331(5) 0.49742(14) 0.0745(7) Uiso 1.000000 R
C13 C 0.38242(18) 0.2214(6) 0.54508(13) 0.0640(6) Uani 1.000000 .
H13 H 0.44837(18) 0.2224(6) 0.57892(13) 0.0768(8) Uiso 1.000000 R
C18 C -0.19460(18) 0.7035(5) 0.34254(14) 0.0600(6) Uani 1.000000 .
H18a H -0.18069(18) 0.8619(5) 0.36338(14) 0.0720(7) Uiso 1.000000 R
H18b H -0.26842(18) 0.6701(5) 0.32647(14) 0.0720(7) Uiso 1.000000 R
C17 C -0.12935(18) 0.5089(6) 0.39050(13) 0.0649(7) Uani 1.000000 .
H17a H -0.17035(18) 0.3855(6) 0.40387(13) 0.0779(8) Uiso 1.000000 R
H17b H -0.07705(18) 0.5697(6) 0.43343(13) 0.0779(8) Uiso 1.000000 R
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'
O 0.05239 0.03377 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C11 C10 C8 122.67(18)
C15 C10 C8 118.53(18)
C15 C10 C11 118.79(18)
C10 C8 O9 119.89(18)
C7 C8 O9 120.49(17)
C7 C8 C10 119.61(17)
C6 C1 C2 118.92(18)
C7 C1 C2 120.94(18)
C7 C1 C6 120.14(19)
C12 C11 C10 120.4(2)
C3 C2 C1 119.9(2)
C5 C6 C1 120.7(2)
C16 C19 O20 134.4(2)
C18 C19 O20 133.2(2)
C18 C19 C16 92.42(17)
C4 C3 C2 120.6(2)
C4 C5 C6 120.3(2)
C5 C4 C3 119.6(2)
C1 C7 C8 109.35(16)
C16 C7 C8 109.83(16)
C16 C7 C1 112.65(14)
C14 C15 C10 120.4(2)
C7 C16 C19 116.94(17)
C17 C16 C19 87.25(18)
C17 C16 C7 117.53(17)
C13 C14 C15 120.6(2)
C13 C12 C11 120.0(2)
C12 C13 C14 119.9(2)
C17 C18 C19 88.75(17)
C18 C17 C16 90.82(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O9 C8 1.209(3)
O20 C19 1.194(3)
C10 C8 1.498(3)
C10 C11 1.387(3)
C10 C15 1.389(3)
C8 C7 1.530(3)
C1 C2 1.388(3)
C1 C6 1.384(3)
C1 C7 1.524(2)
C11 C12 1.392(3)
C2 C3 1.392(3)
C6 C5 1.388(3)
C19 C16 1.524(3)
C19 C18 1.510(3)
C3 C4 1.379(4)
C5 C4 1.371(4)
C7 C16 1.531(2)
C15 C14 1.380(3)
C16 C17 1.551(3)
C14 C13 1.374(4)
C12 C13 1.375(4)
C18 C17 1.524(4)
