#------------------------------------------------------------------------------
#$Date: 2016-07-13 08:41:52 +0200 (Wed 13 de Jul de 2016) $
#$Revision: 184440 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/59/7225913.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_7225913
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 Br N2'
_chemical_formula_sum            'C21 H15 Br N2'
_chemical_formula_weight         375.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-10-28 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            4
_cell_length_a                   5.8446(7)
_cell_length_b                   10.7346(16)
_cell_length_c                   27.540(4)
_cell_measurement_reflns_used    5978
_cell_measurement_temperature    296
_cell_measurement_theta_max      23.44
_cell_measurement_theta_min      2092
_cell_volume                     1727.8(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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            15441
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    2.382
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.156
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0696
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1324P)²+1.3947P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1993
_refine_ls_wR_factor_ref         0.2228
_reflns_number_gt                2662
_reflns_number_total             3917
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra14557d2.cif
_cod_data_source_block           002
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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      'P2(1)2(1)2(1) '
_cod_original_formula_sum        'C21 H15 Br N2 '
_cod_database_code               7225913
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br -0.19422(15) -0.08397(8) 1.00949(3) 0.0734(3) Uani 1 1 d .
N2 N 0.6217(10) 0.1823(5) 0.8524(2) 0.0474(12) Uani 1 1 d .
C13 C 0.3208(12) 0.1459(6) 0.9162(2) 0.0455(14) Uani 1 1 d .
C6 C 0.8882(12) 0.4775(6) 0.8640(2) 0.0481(15) Uani 1 1 d .
C7 C 0.5852(12) 0.0737(6) 0.8229(2) 0.0467(14) Uani 1 1 d .
N1 N 0.7767(10) 0.2682(5) 0.83754(18) 0.0481(12) Uani 1 1 d .
C18 C 0.1278(12) 0.2018(6) 0.9354(2) 0.0472(15) Uani 1 1 d .
H18 H 0.1012 0.2879 0.9297 0.057 Uiso 1 1 calc R
C21 C 0.5715(12) 0.3409(6) 0.9003(2) 0.0479(15) Uani 1 1 d .
H21 H 0.5159 0.3954 0.9248 0.057 Uiso 1 1 calc R
C17 C -0.0271(12) 0.1341(7) 0.9627(2) 0.0528(16) Uani 1 1 d .
H17 H -0.1599 0.1730 0.9756 0.063 Uiso 1 1 calc R
C19 C 0.7463(12) 0.3653(6) 0.8676(2) 0.0463(15) Uani 1 1 d .
C14 C 0.3610(13) 0.0204(6) 0.9251(3) 0.0512(16) Uani 1 1 d .
H14 H 0.4945 -0.0188 0.9127 0.061 Uiso 1 1 calc R
C5 C 0.8273(13) 0.5851(6) 0.8885(3) 0.0592(17) Uani 1 1 d .
H5 H 0.6912 0.5869 0.9073 0.071 Uiso 1 1 calc R
C8 C 0.3787(13) 0.0617(7) 0.7987(3) 0.0555(16) Uani 1 1 d .
H8 H 0.2632 0.1234 0.8018 0.067 Uiso 1 1 calc R
C2 C 1.0891(15) 0.4794(7) 0.8368(3) 0.0626(19) Uani 1 1 d .
H2 H 1.1351 0.4064 0.8199 0.075 Uiso 1 1 calc R
C15 C 0.2035(14) -0.0475(6) 0.9524(3) 0.0564(16) Uani 1 1 d .
H15 H 0.2290 -0.1336 0.9581 0.068 Uiso 1 1 calc R
C20 C 0.4948(12) 0.2230(6) 0.8905(2) 0.0447(14) Uani 1 1 d .
C3 C 1.1618(16) 0.6902(8) 0.8588(3) 0.071(2) Uani 1 1 d .
H3 H 1.2558 0.7623 0.8574 0.085 Uiso 1 1 calc R
C12 C 0.7548(15) -0.0142(7) 0.8189(3) 0.064(2) Uani 1 1 d .
H12 H 0.8968 -0.0040 0.8352 0.077 Uiso 1 1 calc R
C1 C 1.2224(15) 0.5847(7) 0.8339(3) 0.071(2) Uani 1 1 d .
H1 H 1.3571 0.5842 0.8146 0.085 Uiso 1 1 calc R
C9 C 0.3439(16) -0.0434(8) 0.7696(3) 0.066(2) Uani 1 1 d .
H9 H 0.2042 -0.0531 0.7524 0.080 Uiso 1 1 calc R
C4 C 0.9651(15) 0.6908(7) 0.8855(3) 0.065(2) Uani 1 1 d .
H4 H 0.9215 0.7643 0.9024 0.078 Uiso 1 1 calc R
C16 C 0.0143(13) 0.0081(7) 0.9710(2) 0.0535(17) Uani 1 1 d .
C11 C 0.7125(18) -0.1193(7) 0.7901(3) 0.072(2) Uani 1 1 d .
H11 H 0.8261 -0.1823 0.7875 0.086 Uiso 1 1 calc R
C10 C 0.5118(19) -0.1326(8) 0.7659(3) 0.073(2) Uani 1 1 d .
H10 H 0.4871 -0.2041 0.7463 0.087 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'
Br Br -0.2901 2.4595 '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
N1 N2 C20 112.3(5)
N1 N2 C7 118.7(5)
C20 N2 C7 128.1(6)
C18 C13 C14 119.5(6)
C18 C13 C20 119.8(6)
C14 C13 C20 120.5(7)
C5 C6 C2 117.8(6)
C5 C6 C19 120.5(6)
C2 C6 C19 121.7(6)
C12 C7 C8 121.8(6)
C12 C7 N2 119.8(6)
C8 C7 N2 118.5(6)
C19 N1 N2 104.7(5)
C13 C18 C17 120.9(6)
C20 C21 C19 106.7(6)
C18 C17 C16 119.1(7)
N1 C19 C21 110.6(5)
N1 C19 C6 121.4(6)
C21 C19 C6 128.0(6)
C13 C14 C15 119.3(7)
C6 C5 C4 120.2(7)
C7 C8 C9 118.5(7)
C1 C2 C6 121.4(8)
C16 C15 C14 120.8(6)
N2 C20 C21 105.7(6)
N2 C20 C13 124.2(6)
C21 C20 C13 130.0(6)
C4 C3 C1 119.4(7)
C7 C12 C11 118.2(8)
C3 C1 C2 120.3(8)
C10 C9 C8 120.0(7)
C3 C4 C5 120.9(8)
C15 C16 C17 120.4(7)
C15 C16 Br1 120.4(5)
C17 C16 Br1 119.1(6)
C10 C11 C12 121.0(9)
C11 C10 C9 120.5(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C16 1.894(7)
N2 N1 1.356(7)
N2 C20 1.358(8)
N2 C7 1.437(8)
C13 C18 1.382(10)
C13 C14 1.390(9)
C13 C20 1.490(9)
C6 C5 1.385(10)
C6 C2 1.392(11)
C6 C19 1.466(9)
C7 C12 1.373(10)
C7 C8 1.385(10)
N1 C19 1.342(8)
C18 C17 1.384(9)
C21 C20 1.369(9)
C21 C19 1.388(10)
C17 C16 1.393(10)
C14 C15 1.395(10)
C5 C4 1.394(10)
C8 C9 1.399(10)
C2 C1 1.374(10)
C15 C16 1.356(11)
C3 C4 1.365(13)
C3 C1 1.370(12)
C12 C11 1.401(11)
C9 C10 1.375(13)
C11 C10 1.356(14)
