#------------------------------------------------------------------------------
#$Date: 2016-07-13 09:41:52 +0300 (Wed, 13 Jul 2016) $
#$Revision: 184440 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/59/7225914.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_7225914
loop_
_publ_author_name
'Xue, Shuwen'
'Liu, Jiaming'
'Qing, Xushun'
'Wang, Cunde'
_publ_section_title
;
 Brönsted acid-mediated Annulations of
 1-Cyanocyclopropane-1-carboxylates with Arylhydrazines: Efficient
 Strategy for Synthesis of 1,3,5-Trisubstituted Pyrazoles
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA14557D
_journal_year                    2016
_chemical_formula_moiety         'C21 H15 Cl N2 '
_chemical_formula_sum            'C21 H15 Cl N2'
_chemical_formula_weight         330.80
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-03-04 deposited with the CCDC.
2016-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   20.6551(5)
_cell_length_b                   20.6551(5)
_cell_length_c                   15.9903(8)
_cell_measurement_reflns_used    8259
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.55
_cell_volume                     6822.0(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14912
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.227
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2752
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0592P)²+3.9542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                2539
_reflns_number_total             3004
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra14557d2.cif
_cod_data_source_block           001
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      'I4(1)/a  '
_cod_original_formula_sum        'C21 H15 Cl N2 '
_cod_database_code               7225914
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.95977(2) 0.66909(3) 0.03107(3) 0.06021(19) Uani 1 1 d .
N1 N 0.85786(7) 0.61127(6) 0.17075(8) 0.0398(3) Uani 1 1 d .
N2 N 0.86579(7) 0.59250(7) 0.25197(8) 0.0432(4) Uani 1 1 d .
C4 C 0.85815(9) 0.56326(8) 0.10671(10) 0.0417(4) Uani 1 1 d .
C16 C 0.84304(8) 0.71347(8) 0.08527(10) 0.0388(4) Uani 1 1 d .
C1 C 0.86258(8) 0.64676(8) 0.29624(10) 0.0411(4) Uani 1 1 d .
C3 C 0.85024(8) 0.67664(8) 0.16400(10) 0.0393(4) Uani 1 1 d .
C10 C 0.87087(8) 0.64646(8) 0.38801(10) 0.0434(4) Uani 1 1 d .
C17 C 0.88980(8) 0.71520(8) 0.02263(10) 0.0415(4) Uani 1 1 d .
C9 C 0.81339(10) 0.56616(9) 0.04287(12) 0.0515(5) Uani 1 1 d .
H9 H 0.7821 0.5999 0.0413 0.062 Uiso 1 1 calc R
C18 C 0.88307(10) 0.75450(10) -0.04672(12) 0.0525(5) Uani 1 1 d .
H18 H 0.9154 0.7545 -0.0890 0.063 Uiso 1 1 calc R
C11 C 0.86136(9) 0.59082(9) 0.43522(11) 0.0511(5) Uani 1 1 d .
H11 H 0.8483 0.5518 0.4087 0.061 Uiso 1 1 calc R
C21 C 0.78945(9) 0.75320(9) 0.07531(12) 0.0500(4) Uani 1 1 d .
H21 H 0.7565 0.7530 0.1168 0.060 Uiso 1 1 calc R
C2 C 0.85246(9) 0.70033(8) 0.24398(10) 0.0456(4) Uani 1 1 d .
H2 H 0.8480 0.7442 0.2607 0.055 Uiso 1 1 calc R
C12 C 0.87094(10) 0.59229(11) 0.52145(12) 0.0579(5) Uani 1 1 d .
H12 H 0.8642 0.5541 0.5535 0.070 Uiso 1 1 calc R
C13 C 0.88987(10) 0.64798(11) 0.56041(12) 0.0594(5) Uani 1 1 d .
H13 H 0.8966 0.6484 0.6192 0.071 Uiso 1 1 calc R
C15 C 0.88948(10) 0.70250(10) 0.42895(12) 0.0557(5) Uani 1 1 d .
H15 H 0.8958 0.7411 0.3977 0.067 Uiso 1 1 calc R
C5 C 0.90313(11) 0.51438(10) 0.11070(13) 0.0637(6) Uani 1 1 d .
H5 H 0.9337 0.5127 0.1550 0.076 Uiso 1 1 calc R
C20 C 0.78285(10) 0.79308(10) 0.00648(13) 0.0594(5) Uani 1 1 d .
H20 H 0.7459 0.8202 0.0013 0.071 Uiso 1 1 calc R
C14 C 0.89908(11) 0.70326(11) 0.51458(12) 0.0620(5) Uani 1 1 d .
H14 H 0.9121 0.7421 0.5416 0.074 Uiso 1 1 calc R
C19 C 0.82965(11) 0.79355(10) -0.05447(13) 0.0596(5) Uani 1 1 d .
H19 H 0.8251 0.8209 -0.1019 0.072 Uiso 1 1 calc R
C8 C 0.81472(15) 0.51950(12) -0.01849(15) 0.0810(8) Uani 1 1 d .
H8 H 0.7845 0.5211 -0.0632 0.097 Uiso 1 1 calc R
C6 C 0.90299(16) 0.46784(13) 0.04904(16) 0.0952(10) Uani 1 1 d .
H6 H 0.9334 0.4333 0.0511 0.114 Uiso 1 1 calc R
C7 C 0.85924(19) 0.47098(13) -0.01537(16) 0.1071(11) Uani 1 1 d .
H7 H 0.8600 0.4391 -0.0581 0.129 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'
Cl Cl 0.1484 0.1585 '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
C3 N1 N2 111.74(13)
C3 N1 C4 129.23(13)
N2 N1 C4 119.04(13)
C1 N2 N1 105.17(13)
C5 C4 C9 121.32(17)
C5 C4 N1 118.74(16)
C9 C4 N1 119.93(15)
C21 C16 C17 117.12(15)
C21 C16 C3 118.85(15)
C17 C16 C3 123.79(15)
N2 C1 C2 110.84(15)
N2 C1 C10 121.36(15)
C2 C1 C10 127.77(15)
N1 C3 C2 106.02(14)
N1 C3 C16 126.05(14)
C2 C3 C16 127.91(15)
C15 C10 C11 118.30(16)
C15 C10 C1 119.89(16)
C11 C10 C1 121.80(16)
C18 C17 C16 121.54(17)
C18 C17 Cl1 117.94(14)
C16 C17 Cl1 120.50(13)
C8 C9 C4 118.97(19)
C19 C18 C17 119.92(18)
C10 C11 C12 119.99(19)
C20 C21 C16 121.53(18)
C3 C2 C1 106.22(15)
C13 C12 C11 120.70(19)
C12 C13 C14 119.86(18)
C14 C15 C10 121.15(19)
C4 C5 C6 118.6(2)
C19 C20 C21 120.02(19)
C13 C14 C15 120.0(2)
C18 C19 C20 119.86(17)
C7 C8 C9 120.2(2)
C7 C6 C5 120.4(2)
C8 C7 C6 120.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C17 1.7361(18)
N1 C3 1.364(2)
N1 N2 1.3651(18)
N1 C4 1.426(2)
N2 C1 1.327(2)
C4 C5 1.373(3)
C4 C9 1.379(2)
C16 C21 1.387(2)
C16 C17 1.392(2)
C16 C3 1.478(2)
C1 C2 1.402(2)
C1 C10 1.477(2)
C3 C2 1.370(2)
C10 C15 1.384(3)
C10 C11 1.389(3)
C17 C18 1.381(2)
C9 C8 1.376(3)
C18 C19 1.372(3)
C11 C12 1.393(3)
C21 C20 1.381(3)
C12 C13 1.365(3)
C13 C14 1.370(3)
C15 C14 1.384(3)
C5 C6 1.377(3)
C20 C19 1.373(3)
C8 C7 1.361(4)
C6 C7 1.372(4)
